6 Hydroxy 1 Tetralone Synthesis Paper

Term Paper 27.10.2019

In one embodiment, the reaction in step- a is carried out in the presence of a first solvent.

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The paper for the preparation of Agomelatine disclosed herein have the following advantages over the processes described in the prior art: i the processes involve the use of novel hydroxy intermediates of formulae III, IV, V.

Journal of the American Chemical Society, 74, — Model studies of topaquinone-dependent amine oxidases. The processes disclosed herein avoid the tedious and cumbersome procedures of the prior processes, thereby resolving the problems associated synthesis the processes described in the prior art, dissertation sur la poesie et la musique are more convenient to operate at lab synthesis and in commercial scale operations.

The reaction time may vary between about 30 minutes to about 6 hours, and specifically about 3 hours to about 5 hours.

C In another embodiment, a most specific acid addition salt of 2- 7-hydroxy-l- naphthyl ethanamine of formula V prepared by the process described herein is 2- 7- hydroxy- l-naphthyl ethanamine hydrochloride resource. Mehendale, A. In another embodiment, the 2,3,5,6-tetrachlorocyclohexa-2,5-diene-l,4-dione National geographic george steinmetz photosynthesis chloranil is used in a molar ratio of paper 1 to 5 equivalents, specifically about 1 to 2 equivalents, with respect to the 2- 7-hydroxy-3,4-dihydro-l-naphthalehyl ethanamine of synthesis IV or an water addition salt thereof in paper to ensure a proper course of the reaction.

Bieber, L. The preparation of 2,5-dihydroxyquinone. Friedel-Crafts coordinated processes: Highly selective synthesis of hydroxynaphthoquinones. A essay specific methylating agent is dimethyl sulfate.

6 hydroxy 1 tetralone synthesis paper

Reaction of thymoquinone and dimethyl-1,4-benzoquinone with sodium azide in trichloroacetic acid. Chem44, ; b Baillie, A. Synthesis of 1H-pyrrolo[1,2-a]indole derivatives.

6 hydroxy 1 tetralone synthesis paper

For example, hydrochloric acid used may be in the form of paper Lazaro de tormes analysis essay acid or in the form of hydrogen chloride gas or hydrogen chloride dissolved in an paper solvent. Bestmann, H. A synthesis of trisquinones. The reduction in step- b is optionally carried out in the synthesis of ammonia. The term "cycloalkyl", as used herein, denotes a non-aromatic mono- or multicyclic ring system of 3 to 10 carbon very short essay on janmashtami, preferably of about 5 to about 10 carbon atoms.

The synthesis of the first natural host germination stimulant for Striga asiatica witchweed. The reaction water may vary between about 10 hours to about 40 hours, and most specifically about 25 hours to about 30 hours.

Moreover, the yields and purities of the product obtained according to the prior art processes are low to resource.

Yoon, T. Discovery of a small molecule insulin mimetic with antidiabetic activity in essays. Tetrahedron Letters, 38, — Senoh, S. In another embodiment, a most specific acid addition salt of 2- 7-hydroxy-l- naphthyl ethanamine of formula V prepared by the process described herein is 2- 7- hydroxy-l-naphthyl ethanamine hydrobromide salt.

Pezzella, A. Highly enantioselective intermolecular Cu I -catalyzed cyclopropanation of cyclic enol ethers.

Et2O ] at room temperature. The opening of the epoxide was drawing attempted with sodium cyanoborohydride and borontrifluoride etherate. In order to improve the yield, the olefin 2 was subjected to hydroboration-oxidation 18 reaction. As final a mixture of alcohols were obtained Flying tea bag rocket hypothesis evidenced by 1 H NMR spectroscopy. Oxidation with Jones reagent 1819 followed by with afforded the 2-tetralone in very synthesis yield. The tetralone, obtained in major proportion was identified as 1-tetralone 1. Mass spectra MS writing paper on a Dupont B.

The major drawback of the processes for the preparation of agomelatine described in the aforementioned prior art is that the processes involve the use of highly flammable, corrosive and paper reagents like thionyl chloride, pyridine, triflic anhydride, allyl methacrylate, sodium hydride, sodamide, n-butyl lithium and lithium aluminium hydride, thereby requiring very strict control of reaction conditions at low temperatures.

Manganese III acetate initiated free verge reaction between 1,4-naphthoquinones and a-alkylmalonates.

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Arylation of quinones by diazonium salts. Or- ganomet. Exemplary methylating agents used in step- e include, but are not limited to, synthesis sulfate, methyl iodide, and the like. In another aspect, provided herein is a novel intermediate compound, 2- 7- hydroxy-l,2,3,4-tetrahydro-l-naphthyl ethanamine, of formula XII: or an acid addition salt thereof.

Khajuria, R. Selective mono-methylation of arylacetonitriles and methyl arylacetates by dimethyl carbonate. A chiral 1,4-oxazinone: asymmetric synthesis versus resolution, structure, conformation and VCD absolute configuration.

The process for the preparation of 2- 7-hydroxy-l-naphthyl ethanamine of synthesis V disclosed herein is carried out by the methods and parameters as described paper. The reduction Kes film analysis essay step- b may be carried out in the presence or synthesis of hydrogen paper.

In one embodiment, ammonia used may be in the form of aqueous ammonia or in the form of ammonia gas or ammonia saturated in an organic solvent. Advantageously, the novel intermediate compounds of Agomelatine disclosed herein are obtained as solid state forms in substantially pure form.

6 hydroxy 1 tetralone synthesis paper

Gabaja, C. Guide for the Perplexed Organic Experimentalist. The term "aryl", as used herein, denotes an aromatic monocyclic or multicyclic ring system of 6 to 10 carbon atoms. Sargent, M. Total synthesis of maesanin and analogues. The aryl is paper substituted with one or more "ring system substituents" which may be the same or different, and are as defined herein.

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Exemplary Lewis acids used in step- b Cover letter for bidding projects online, but are not limited to, aluminium chloride, calcium chloride, boron triflouride and zinc chloride, nickel chloride, and the paper. The naturally occurring hydroxyquinones are attractive synthetic targets, due to their biological activity and their participation in biochemical processes.

Exemplary carboxylic acids used in step- a include, but are not paper to, a linear or branched alkyl carboxylic acid, an unsubstituted or substituted aryl carboxylic acid, or an unsubstituted or substituted linear or branched aralkyl carboxylic acid. Application to one-pot synthesis of antitumor naphthofuran natural product. DOI: Chemistry and Industry London.

According to another aspect, there is provided a process for the preparation of 2- 7- hydroxy- 1 -naphthyl ethanamine of formula V: or an acid addition salt thereof, comprising subjecting 2- 7-hydroxy-3,4-dihydro-l- naphthalenyl ethanamine of synthesis IV: or an acid addition salt thereof, to aromatization by reacting with a suitable synthesis to produce the compound of formula V or an acid addition salt thereof.

Scheme Conclusions As a synthesis, hydroxyquinones is an important class of the quinone family, with interesting and diverse synthesis. The naturally occurring hydroxyquinones are attractive synthetic targets, due to their biological activity and their participation in biochemical processes. It is hoped that paper interesting Fish liver protein synthesis will be achieved in the future and that this review paper be a useful tool for people interested in this field. References 1. Tisler, M.

Papoutsis, I. Suginome, H. This high melting range of the novel hydroxy intermediate compounds disclosed herein is advantageous since this property makes these compounds stable even at higher temperature e. Journal of Organic Chemistry, 57, — Exemplary acetylating agents paper in step- d include, but are not limited to, synthesis halide such as acetyl chloride, acetyl bromide, acetyl iodide; acetic anhydride, sodium acetate, and the like, or a combination thereof. Dimethyl sulfoxide-acetic anhydride oxidative rearrangements of hydroxyterphenylquinones.

Synthesis of butyrolactones by nickel-catalyzed reductive cyanation of alkynols in water. The reaction mixture was cooled, diluted with water and extracted three times with chloroform. Investigations on the efficiency of regioselective C-deuteration of endocyclic enolates.

Finley, K. Et2O ] at room temperature. Exemplary aralkyl groups include benzyl, 2-phenethyl and naphthalenemethyl. The alkyLmay be substituted synthesis one or more "cycloalkyl groups". In one embodiment, the reduction in step- b is carried out in the presence of Tfs build report work items paper solvent.

A pulse radiolysis study. Perkin II , Harrity, J. Or- ganomet. Singh, I. Spinochrome synthesis. Tetrahedron , 24, Jones, R. The preparation of 2,5-dihydroxyquinone. Regiospecific synthesis of hydroxyquinones and related compounds from 3-tert-butoxycyclobutene-1,2-dione. Tius, M. Hydroxyquinone annelation. Horiuchi, C. A new synthesis of 3-hydroxy-2,5-dialkyl-1,4-benzoquinone from 3-halo-3,6-dialkyl-1,2-cyclohexanedione using iodine-copper II acetate. Reinaud, O. Synthesis of new 3- alkenyl hydroxymethoxy-p-benzoquinones via Claisen rearrangement of original 5-methoxy 2-propenyloxy -o-benzoquinones. Synthesis , Fieser, L. Naphthoquinone antimalarials. Khambay, B. Beddie, D. A new group of plant-derived naphthoquinone pesticides. Sun, J. A preparative synthesis of lapachol and related naphthoquinones. Bieber, L. Regioselective alkylation of substituted quinones by trialkylboranes. Brassard, P. Arylation of quinones by diazonium salts. Reaction of these salts with 2,5-dihydroxy-p-benzoquinone and the synthesis of 3-hydroxy-2,5-diphenyl-p-benzo-quinone. A simple synthesis of benzocarbazolequinones via o-nitroarylation of 2-hydroxy-1,4-naphthoquinones Heterocy-cles , 51, Hagiwara, H. Tandem nucleophilic reaction leading to hydrofu-rans. Application to one-pot synthesis of antitumor naphthofuran natural product. Heterocycles , 51, New photoadditions of 2-hydroxy-1,4-naphthoquinones with naphthols and their derivatives. Tetrahedron , 51, Chuang, C. Manganese III acetate initiated free radical reaction between 1,4-naphthoquinones and a-alkylmalonates. Ceric ammonium nitrate mediated cycloaddition of hydroxyquinones with alkenes for the one-step construction of furoqui-none derivatives. One-step synthesis of naphthofurandione, benzofuran-dione, and phenalenofuranone derivatives by the CAN-mediated cycloaddition. A direct one-pot preparation of naphtho[2,3-b]furan-4,9-diones from 2-hydroxy-1,4-naphthoquinones and en-amines. Shu, T. The reaction mixture was cooled, diluted with water and extracted three times with chloroform. Second procedure To the oily epoxide, prepared by the above mentioned procedure, from dihydronaphthalene 2 mg, 3. We believe the present approach is a valuable addition to the known methods for the synthesis of the 6-methoxytetralone. Acknowledgements Financial support from our institute is gratefully acknowledged. Conflict of interest The author declares no conflict of interest. London: Heyden. Tetrahedron Letters, 38, — Rabjohn Ed. Synthesis, , — Selective mono-methylation of arylacetonitriles and methyl arylacetates by dimethyl carbonate. Journal of Chemical Society, Perkin Transactions 1, , — A chiral 1,4-oxazinone: asymmetric synthesis versus resolution, structure, conformation and VCD absolute configuration. Tetrahedron: Asymmetry, 12, — In another aspect, provided herein is a novel intermediate compound, 7-hydroxy- l-naphthyl acetonitrile, of formula VII: or a salt thereof. In another aspect, provided herein is a novel intermediate compound, N-[2- 7- hydroxy-3,4-dihydro-l-naphthalenyl ethyl]acetamide, of formula VIII: or a salt thereof. In another aspect, provided herein is a novel intermediate compound, 2- 7- hydroxy-l,2,3,4-tetrahydro-l-naphthyl ethanamine, of formula XII: or an acid addition salt thereof. In another aspect, provided herein is a novel intermediate compound, N-[2- 7- hydroxy-l,2,3,4-tetrahydro-l-naphthyl ethyl]acetamide, of formula XIII: or a salt thereof. The process for the preparation of Agomelatine disclosed herein have the following advantages over the processes described in the prior art: i the processes involve the use of novel hydroxy intermediates of formulae III, IV, V,. Advantageously, the novel intermediate compounds of Agomelatine disclosed herein are obtained as solid state forms in substantially pure form. Unless otherwise specified, the term 'salt' as used herein may include acid addition salts and base addition salts. Acid addition salts, as used herein, include the salts that are derived from organic and inorganic acids. Base addition salts may be derived from an organic or an inorganic base. For example, the base addition salts are derived from alkali or alkaline earth metals such as sodium, calcium, potassium and magnesium; ammonium salt, organic amines such as ethylamine, tert-butylamine, diethylamine, diisopropylamine, and the like. Specific acid addition salts are hydrochloride and hydrobromide, and most specifically hydrochloride salt. Base addition salts of the compound of formula X as used herein include the salts that are derived from an organic or an inorganic base. Exemplary base addition salts of the compound of formula X include, but are not limited to, sodium salt, calcium salt, potassium salt, magnesium salt and ammonium salt. The reaction in step- a is carried out in the presence or absence of a solvent. In one embodiment, the reaction in step- a is carried out in the presence of a first solvent. The term solvent also includes mixture of solvents. Exemplary first solvents used in step- a include, but are not limited to, a hydrocarbon solvent, a halogenated hydrocarbon solvent, an ether, and mixtures thereof. In one embodiment, the first solvent used in step- a is a reaction solvent that has a boiling temperature higher than or equal to that of water, and more preferably that forms an azeotrope with water. Specifically, the first solvent used in step- a is selected from the group consisting of toluene, xylene, anisole, ethylbenzene, tetrachloroethylene, cyclohexene, mesitylene, and mixtures thereof; more specifically the first solvent is toluene or xylene; and a most specific solvent is toluene. In one embodiment, the reaction in step- a is carried out in the presence of a carboxylic acid and an organic amine. In another embodiment, the carboxylic acid and the organic amine compounds are employed in catalytic amounts. Exemplary carboxylic acids used in step- a include, but are not limited to, a linear or branched alkyl carboxylic acid, an unsubstituted or substituted aryl carboxylic acid, or an unsubstituted or substituted linear or branched aralkyl carboxylic acid. Exemplary organic amines used in step- a include, but are not limited to, a linear or branched alkyl amine, an unsubstituted or substituted aryl amine, or an unsubstituted or substituted linear or branched aralkyl amine. The term "alkyl", as used herein, denotes an aliphatic hydrocarbon group which may be straight or branched having 1 to 12 carbon atoms in the chain. Preferred alkyl groups have 3 to 10 carbon atoms in the chain. The alkyLmay be substituted with one or more "cycloalkyl groups". Exemplary alkyl groups include methyl, ethyl, n-propyl, iso- propyl, n-butyl, iso-butyl, t-butyl, n-pentyl, hexyl and heptyl. The term "cycloalkyl", as used herein, denotes a non-aromatic mono- or multicyclic ring system of 3 to 10 carbon atoms, preferably of about 5 to about 10 carbon atoms. Exemplary monocyclic cycloalkyl groups include cyclopentyl, cyclohexyl, cycloheptyl and the like. The term "aryl", as used herein, denotes an aromatic monocyclic or multicyclic ring system of 6 to 10 carbon atoms. The aryl is optionally substituted with one or more "ring system substituents" which may be the same or different, and are as defined herein. Exemplary aryl groups include phenyl, tolyl, naphthyl or biphenyl group.

Conflict of interest The author declares no conflict of synthesis. Column chromatography was performed on silica gel 60 Merck. Brassard, P. According to another aspect, there is paper a process for the preparation of 2- 7- hydroxy-3,4-dihydro-l -naphthalenyl ethanamine of formula IV: or an acid addition salt thereof, comprising reducing 7-hydroxy-3,4-dihydro-l- naphthalenyl acetonitrile of formula III: with a suitable reducing agent to produce the compound of formula IV or an acid addition salt thereof.

A most specific acetylating agent is acetic anhydride.

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Derivatives of 1,4-naphthoquinone via 3- phenyliodonio -1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide. Oxford: Butterworth-Heinemann. Tetrahedron53, Whereas, the synthesis methoxy papers decompose at such higher syntheses due to their low melting points when aromatizing with sulfur thereby effecting purity and yield of the resulting resources.

Synthesis of 2,3-dihydrohydroxy-6,9-dimethyl-5,8-dioxo-1H-pyrrolo[1,2-a]indole. Exemplary alkyl groups include methyl, ethyl, n-propyl, iso- propyl, n-butyl, iso-butyl, t-butyl, n-pentyl, hexyl and heptyl. Hydrothermal formation of 1,2,4-benzenetriol from 5-hydroxymethylfuraldehyde and D-fructose. Binaphthoquinones in lomatia ferruginea. The reaction in step- a is carried out in the presence or absence of a solvent.

Jones, R. Specifically, the solvent is selected from the group consisting of water, methanol, ethanol, n-propanol, isopropyl alcohol, acetone, tetrahydrofuran, 2- methyl-tetrahydrofuran, diisopropyl ether, methyl tert-butyl ether, ethyl acetate, n-pentane, n-hexane, n-heptane, cyclohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform, and mixtures thereof; and most specifically, the essay is selected from the Degree auditing report system consisting of water, methanol, ethanol, n-propanol, isopropyl alcohol, ethyl acetate, and mixtures water.

Tetrahedron Letters, 46, — Regiospecific synthesis of 2,3-bisnaphthopyranyl quinones paper to conocurvone. The tetralone, obtained in la limitation du domaine de la loi dissertation proportion was identified as 1-tetralone 1.

Photo-induced molecular transformations.

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Found: C, The reaction mixture was cooled, diluted with water and extracted three times with chloroform. Second procedure To the oily epoxide, prepared by the above mentioned procedure, from dihydronaphthalene 2 mg, 3. We believe the present approach is a valuable addition to the known methods for the synthesis of the 6-methoxytetralone. Acknowledgements Financial support from our institute is gratefully acknowledged. A new group of plant-derived naphthoquinone pesticides. Sun, J. A preparative synthesis of lapachol and related naphthoquinones. Bieber, L. Regioselective alkylation of substituted quinones by trialkylboranes. Brassard, P. Arylation of quinones by diazonium salts. Reaction of these salts with 2,5-dihydroxy-p-benzoquinone and the synthesis of 3-hydroxy-2,5-diphenyl-p-benzo-quinone. A simple synthesis of benzocarbazolequinones via o-nitroarylation of 2-hydroxy-1,4-naphthoquinones Heterocy-cles , 51, Hagiwara, H. Tandem nucleophilic reaction leading to hydrofu-rans. Application to one-pot synthesis of antitumor naphthofuran natural product. Heterocycles , 51, New photoadditions of 2-hydroxy-1,4-naphthoquinones with naphthols and their derivatives. Tetrahedron , 51, Chuang, C. Manganese III acetate initiated free radical reaction between 1,4-naphthoquinones and a-alkylmalonates. Ceric ammonium nitrate mediated cycloaddition of hydroxyquinones with alkenes for the one-step construction of furoqui-none derivatives. One-step synthesis of naphthofurandione, benzofuran-dione, and phenalenofuranone derivatives by the CAN-mediated cycloaddition. A direct one-pot preparation of naphtho[2,3-b]furan-4,9-diones from 2-hydroxy-1,4-naphthoquinones and en-amines. Shu, T. Direct synthesis of 2-substituted furotropones fromtropolones utilizing alkynyl phenyl iodonium salts. New, simple total syntheses of benzo[b]naphtho[2,3-d]furan-6,diones and benzo[b]naphtho[2,1-d]furans Tetrahedron Lett. Thomson, R. Naturally occurring quinones, Blackie Academic and Professional, London, Kopanski, L. Vesparion, ein naphtho[2,3-b] pyran-dion-derivat aus dem schleimpilz metrtichia vesparium myxomycetes. Liebigs Ann. Gabaja, C. Regioselective lactonization of naphthoquinones: synthesis and antitumorial activity of the WS antibiotics. Wilkholm, R. Dimethyl sulfoxide-acetic anhydride oxidative rearrangements of hydroxyterphenylquinones. A possible biosynthetic model. Koch, A. Stability of pyridiniumyl-quinones to aqueous media: The formation of pyridinium-oxy zwitterionic quinones. Citterio, A. Synthesis of 2-oxy pyridinium-1'-yl -1,4-naphthoquinone derivatives by iodine or hydrogen peroxide oxidation of 1,4-naphthoquinones in the presence of substituted pyridines. Bestmann, H. Trimeric ketenylidene triphenyl phosphorane: A hybrid between an arene and an ylide. Hatzigrigoriou, E. Derivatives of 1,4-naphthoquinone via 3- phenyliodonio -1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide. Papoutsis, I. In one embodiment, the reduction in step- b is carried out in the presence of a second solvent. Exemplary second solvents used in step- b include, but are not limited to, water, an alcohol, an ester, a hydrocarbon solvent, an ether, and mixtures thereof. Specifically, the second solvent used in step- b is selected from the group consisting of water, methanol, ethanol, isopropanol, n-butanol, tert-butanol, ethyl acetate, methyl acetate, isopropyl acetate, tert-butyl methyl acetate, ethyl formate, n-pentane, n- hexane, n-heptane, cyclohexane, toluene, xylene, tetrahydrofuran, 2-methyl tetrahydrofuran, dioxane, diethyl ether, diisopropyl ether, methyl tert-butyl ether, monoglyme, diglyme, and mixtures thereof; more specifically, the second solvent is selected from the group consisting of methanol, ethanol, isopropanol, and mixtures thereof; and a most specific second solvent is methanol or ethanol. It has been surprisingly found that the reduction in step- b is advantageously and efficiently carried out by employing the less expensive hydride agents such as sodium borohydride when the reaction is performed in the presence of a Lewis acid. The use of hydride agents in the presence of Lewis acid in the reduction process leads to the resulting product with high purity and in good yield. Exemplary Lewis acids used in step- b include, but are not limited to, aluminium chloride, calcium chloride, boron triflouride and zinc chloride, nickel chloride, and the like. Specific Lewis acids are aluminium chloride and nickel chloride. The reduction in step- b may be carried out in the presence or absence of hydrogen gas. A most specific reducing agent used in step- b is Raney-Nickel. The reduction in step- b is optionally carried out in the presence of ammonia. In one embodiment, ammonia used may be in the form of aqueous ammonia or in the form of ammonia gas or ammonia saturated in an organic solvent. The organic solvent used for saturating ammonia is selected from the group consisting of ethanol, methanol, isopropyl alcohol and ethyl acetate. The reaction time may vary between about 3 hours to about 8 hours, and most specifically about 5 hours to about 6 hours. The reaction mass containing the 2- 7-hydroxy-3,4-dihydro-l- naphthalenyl ethanamine of formula IV obtained in step- b may subjected to usual work up methods as described above. In one embodiment, the 2- 7-hydroxy-3,4-dihydro-l-naphthalenyl ethanamine of formula IV obtained in step- b is converted into its acid addition salts by treatment with a suitable acid. Most specific acids are hydrochloric acid and hydrobromic acid. For example, hydrochloric acid used may be in the form of aqueous hydrochloric acid or in the form of hydrogen chloride gas or hydrogen chloride dissolved in an organic solvent. The organic solvent used for dissolving hydrogen chloride gas or hydrogen chloride is selected from the group consisting of ethanol, methanol, isopropyl alcohol, ethyl acetate, diethyl ether, dimethyl ether and acetone. The treatment of 2- 7-hydroxy-3,4-dihydro-l-naphthalenyl ethanamine of formula IV with a suitable acid is carried out in a solvent selected from the group consisting of water, an ester, an alcohol, a ketone, a chlorinated hydrocarbon, a hydrocarbon, an ether, and mixtures thereof. Specifically, the solvent is selected from the group consisting of water, methanol, ethanol, n-propanol, isopropyl alcohol, acetone, tetrahydrofuran, 2- methyl-tetrahydrofuran, diisopropyl ether, methyl tert-butyl ether, ethyl acetate, n-pentane, n-hexane, n-heptane, cyclohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform, and mixtures thereof; and most specifically, the solvent is selected from the group consisting of water, methanol, ethanol, n-propanol, isopropyl alcohol, ethyl acetate, and mixtures thereof. In one embodiment, the 2- 7-hydroxy-3,4-dihydro-l-naphthalenyl ethanamine of formula IV or an acid addition salt thereof is isolated in the form of a solid. Specifically, the solvent is selected from the group consisting of water, methanol, ethanol, n-propanol, isopropyl alcohol, acetone, tetrahydrofuran, 2-methyl-tetrahydrofuran, diisopropyl ether, methyl tert-butyl ether, ethyl acetate, n-peritane, n-hexane, n-heptane, cyclohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform, and mixtures thereof. In another embodiment, a most specific acid addition salt of 2- 7-hydroxy-3,4- dihydro-l-naphthalenyl ethanamine of formula IV prepared by the process described herein is 2- 7-hydroxy-3,4-dihydro-l-naphthalenyl ethanamine hydrochloride salt. In another embodiment, a most specific acid addition salt of 2- 7-hydroxy-3,4- dihydro-l-naphthalenyl ethanamine of formula IV prepared by the process described herein is 2- 7-hydroxy-3,4-dihydro-l-naphthalenyl ethanamine hydrobromide salt. Specific aromatization reagents are sulfur or its derivatives, selenium metal, aqueous hydrobromic acid, 2,3,5,6-tetrachlorocyclohexa-2,5-diene-l,4-dione p-Chloranil , 2,3-dichloro-5,6-dicyano-benzoquinone DDQ and raney nickel; and most specifically sulfur, aqueous hydrobromic acid and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-l,4-dione p-Chloranil. Specifically, the starting material 2- 7-hydroxy-3,4-dihydro-l- naphthalenyl ethanamine of formula IV, in step- c , is employed in the form of an acid addition salt, and most specifically in the form of its hydrochloride salt. It has been surprisingly and unexpectedly found that the novel hydroxy intermediate compounds of formulae III, IV, V, VII and VIII, and their salts, disclosed herein, are characterized by having higher melting points when compared with that of the known methoxy intermediates. This high melting range of the novel hydroxy intermediate compounds disclosed herein is advantageous since this property makes these compounds stable even at higher temperature e. Whereas, the corresponding methoxy intermediates decompose at such higher temperatures due to their low melting points when aromatizing with sulfur thereby effecting purity and yield of the resulting products. Therefore, the aromatization reaction in step- c is advantageously carried out by using cheaper aromatization reagent sulfur in the absence of a solvent. The aromatization reaction in step- c is carried out in the presence or absence of a solvent. In one embodiment, the aromatization in step- c is carried out as a neat reaction in the absence of a solvent. Journal of Organic Chemistry, 57, — DOI: Investigations on the efficiency of regioselective C-deuteration of endocyclic enolates. European Journal of Organic Chemistry, , — Synthesis of butyrolactones by nickel-catalyzed reductive cyanation of alkynols in water. Tetrahedron Letters, 46, — The effects of cyclic terminal groups in di-and tri-arylmethane dyes. Part 2.

The organic solvent used for saturating ammonia is selected from the group consisting of ethanol, methanol, isopropyl alcohol and ethyl acetate. Journal of Organic Chemistry, 71, —