138113-08-3

Basic information

• Product Name: 7-Methoxy-1-naphthylacetonitrile
• Synonyms: 1-Cyanomethyl-7-methoxynaphthalene;2-(7-Methoxy-1-naphthyl)acetonitrile;7-Methoxy-1-naphthaleneacetinitrile;7-Methoxy-1-naphthylacetonitrile;2-(7-methoxynaphthalen-1-yl)acetonitrile;Agomelatine Intermediate 1;N-[2-(7-Methoxy-1-naphthyl)ethyl]acetaMide;AgoMelatine interMediate A
• CAS NO: 138113-08-3
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 197.23
• EINECS: -0
• Product Categories: Aromatics Compounds;Aromatics;Intermediate of Agomelatine
• Mol File: 138113-08-3.mol

Chemical Properties

• Melting Point: 81-83°C
• Boiling Point: 374.3 °C at 760 mmHg
• Flash Point: 157.7 °C
• Appearance: tan solid
• Density: 1.135 g/cm³
• Vapor Pressure: 8.4E-06mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: slightly sol. in Methanol
• CAS DataBase Reference: 7-Methoxy-1-naphthylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Methoxy-1-naphthylacetonitrile(138113-08-3)
• EPA Substance Registry System: 7-Methoxy-1-naphthylacetonitrile(138113-08-3)

Safety Data

• RIDADR: UN 3439 6.1/PG III
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 138113-08-3(Hazardous Substances Data)

Usage

Chemical Properties

Tan Solid

InChI:InChI=1/C13H11NO/c1-15-12-6-5-10-3-2-4-11(7-8-14)13(10)9-12/h2-6,9H,7H2,1H3

Synthetic route

+ 1-chloromethyl-7-methoxynaphthalene → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

sodium cyanide (773837-37-9) + 1-bromomethyl-7-methoxynaphthalene (91571-02-7) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
In dimethyl sulfoxide at 140 - 145℃; for 3h;	99%

2-(7-methoxy-3,4-dihydronaphthalen-1-yl)acetonitrile (861960-34-1) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; under 15.0015 Torr; for 6h; Catalytic behavior; Solvent; Pressure; Green chemistry;	95%
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; under 15.0015 Torr; for 5h; Solvent; Pressure; Time;	93%
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; under 15.0015 Torr; for 5h; Pressure; Solvent;	93%

7-Methoxy-1-tetralone (6836-19-7) + cyanoacetic acid (372-09-8) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With 5%-palladium/activated carbon In dimethyl sulfoxide at 20℃; for 4.5h; Molecular sieve;	95%

1-cyano-1-(7-methoxy-3,4-dihydro-1-naphthyl)methanol acetate → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With acetic acid for 12h; Reflux;	95%

1-bromo-7-methoxy-naphthalene (83710-61-6) + cyanomethyl bromide (590-17-0) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Stage #1: 1-bromo-7-methoxy-naphthalene With iodine; magnesium In tetrahydrofuran at 5 - 38℃; for 2.08333h; Stage #2: cyanomethyl bromide In tetrahydrofuran at 0 - 55℃; for 2h; Temperature; Solvent; Concentration;	94.6%

1-cyano-1-(7-methoxy-3,4-dihydro-1-naphthyl)methanol formate → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With formic acid In toluene for 12h; Reflux;	94%

(7-hydroxy-1-naphthyl)acetonitrile (1079774-32-5) + dimethyl sulfate (77-78-1) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With potassium carbonate In acetone for 3h; Reflux;	92.9%

1-cyano-1-(7-methoxy-3,4-dihydro-1-naphthyl)methanol propionate → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
In toluene for 12h; Reflux;	92%

1-cyano-1-(7-methoxy-3,4-dihydro-1-naphthyl)methanol benzoate → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With acetic acid In toluene for 12h; Reflux;	92%

2-(2-methoxynaphthalen-8-yl)acetamide (138113-07-2) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With trichlorophosphate In dichloromethane; N,N-dimethyl-formamide at 85℃; for 2h;	91%
With triethylamine; trifluoroacetic anhydride In tetrahydrofuran for 1h; Ambient temperature;	83%
With triethylamine; trifluoroacetic anhydride In tetrahydrofuran at 20℃; Cooling with ice;	80%

1-cyano-1-(7-methoxy-3,4-dihydro-1-naphthyl)methanol butyrate → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With butyric acid In ethyl acetate for 12h; Reflux;	90%

1-cyano(7-methoxy-3,4-dihydronaphthalen-1-yl)methyl 4-chlorobenzoate → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With acetic acid for 12h; Reflux;	90%

1-cyano-1-(7-methoxy-3,4-dihydro-1-naphthyl)methanol isobutyrate → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With acetic acid for 12h; Reflux;	89%

1-hydroxy-7-methoxy-3,4-dihydro-1-naphthylacetonitrile (360766-78-5) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 1h; Heating;	88.2%

1-cyano(7-methoxy-3,4-dihydronaphthalen-1-yl)methyl p-nitrobenzoate → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With acetic acid In toluene for 12h; Reflux;	88%

1-(cyanomethyl)-7-methoxynaphthalen-2-yltrifluoromethanesulphonate → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; triethylamine In ethanol at 20℃; under 3000.3 Torr; for 20h;	67%

(7-methoxy-1,2-dihydro-1-naphthyl)acetonitrile (1384168-59-5) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
With chloranil In toluene at 80℃; for 2.5h;	61%

2-(1-hydroxyl-7-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetonitrile (59081-65-1) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90.7 percent / DDQ / CH2Cl2 / 20 °C 2: 88.2 percent / TsOH*H2O / benzene / 1 h / Heating View Scheme

7-Methoxy-1-tetralone (6836-19-7) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2: 90.7 percent / DDQ / CH2Cl2 / 20 °C 3: 88.2 percent / TsOH*H2O / benzene / 1 h / Heating View Scheme
Multi-step reaction with 6 steps 1.1: zinc / iodine / toluene / Reflux 1.2: Reflux 1.3: 3 h / Reflux 2.1: sulfur / ethyl acetate / 10 h / 215 °C 3.1: sodium hydroxide; water / ethanol / 3 h / 20 °C 4.1: thionyl chloride / dichloromethane / 2 h / Reflux 5.1: ammonia / ethyl acetate; water / Cooling with ice 6.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: ammonium acetate / toluene / Azeotropic reflux 2: sulfur / 0.17 h / 175 °C View Scheme

2-(7-methoxynaphthalen-1-yl)acetic acid (6836-22-2) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 / CHCl3 / 2 h / Heating 2: conc. aq. NH3 / diethyl ether / 0.5 h 3: 83 percent / Et3N, (CF3CO)2O / tetrahydrofuran / 1 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / CHCl3 2: aq. NH4OH / diethyl ether / 0 °C 3: (CF3CO)2O / tetrahydrofuran / 0 °C View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 2 h / Reflux 2: ammonia / ethyl acetate; water / Cooling with ice 3: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 35 - 40 °C 2: ammonia / toluene / 0 - 5 °C / pH 10 - 11 3: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 2 h / 85 °C View Scheme

(7-methoxy-1-naphthyl)acetic acid chloride (6836-23-3) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. aq. NH3 / diethyl ether / 0.5 h 2: 83 percent / Et3N, (CF3CO)2O / tetrahydrofuran / 1 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: aq. NH4OH / diethyl ether / 0 °C 2: (CF3CO)2O / tetrahydrofuran / 0 °C View Scheme

ethyl 2-(7-methoxynaphthalen-1-yl)acetate (6836-21-1) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; water / ethanol / 3 h / 20 °C 2: thionyl chloride / dichloromethane / 2 h / Reflux 3: ammonia / ethyl acetate; water / Cooling with ice 4: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice View Scheme

ethyl (1,2,3,4-tetrahydro-7-methoxy-1-naphthyl)acetate (27532-26-9) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: sulfur / ethyl acetate / 10 h / 215 °C 2: sodium hydroxide; water / ethanol / 3 h / 20 °C 3: thionyl chloride / dichloromethane / 2 h / Reflux 4: ammonia / ethyl acetate; water / Cooling with ice 5: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice View Scheme

1-methyl-7-methoxynaphthalene (2825-01-6) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 1.5 h / Reflux; Microwave irradiation 2: dimethyl sulfoxide / 3 h / 140 - 145 °C View Scheme

(7-methoxy-4-oxo-1,2,3,4-tetrahydro-1-naphthyl)acetonitrile (1384168-60-8) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aluminum isopropoxide / isopropyl alcohol / 20 °C / Reflux 1.2: 1 h / Dean-Stark; Reflux 2.1: chloranil / toluene / 2.5 h / 80 °C View Scheme

O-ethyl S-2-(4-methoxyphenyl)-2-oxoethyl carbonodithioate (93624-01-2) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ethyl acetate / 0.25 h / Reflux; Inert atmosphere 1.2: Reflux 2.1: chlorobenzene / 0.25 h / Reflux; Inert atmosphere 2.2: Reflux 3.1: aluminum isopropoxide / isopropyl alcohol / 20 °C / Reflux 3.2: 1 h / Dean-Stark; Reflux 4.1: chloranil / toluene / 2.5 h / 80 °C View Scheme

S-[1-(cyanomethyl)-4-(4-methoxyphenyl)-4-oxobutyl]-O-ethyl dithiocarbonate (1384168-58-4) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: chlorobenzene / 0.25 h / Reflux; Inert atmosphere 1.2: Reflux 2.1: aluminum isopropoxide / isopropyl alcohol / 20 °C / Reflux 2.2: 1 h / Dean-Stark; Reflux 3.1: chloranil / toluene / 2.5 h / 80 °C View Scheme

[7-Methoxy-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-acetic acid (63319-95-9) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: palladium on activated charcoal; sodium carbonate; acrylic acid / water / 100 - 105 °C 2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 35 - 40 °C 3: ammonia / toluene / 0 - 5 °C / pH 10 - 11 4: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 2 h / 85 °C View Scheme

ethyl (7-methoxy-1,2,3,4-tetrahydro-1-naphthalenylidene)acetate (6836-20-0) → (7-methoxy-1-naphthyl)acetonitrile (138113-08-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium hydroxide / tert-butyl alcohol / 2 h / 85 - 90 °C 2: palladium on activated charcoal; sodium carbonate; acrylic acid / water / 100 - 105 °C 3: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 35 - 40 °C 4: ammonia / toluene / 0 - 5 °C / pH 10 - 11 5: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 2 h / 85 °C View Scheme

(7-methoxy-1-naphthyl)acetonitrile (138113-08-3) → 2-(7-methoxy-3,4-dihydronaphthalen-1-yl)acetonitrile (861960-34-1)

Conditions	Yield
With allyl methacrylate; 5% active carbon-supported ruthenium In toluene at 80℃; for 4h; Catalytic behavior; Temperature; Solvent;	96.2%

(7-methoxy-1-naphthyl)acetonitrile (138113-08-3) → 2-(7-methoxynaphth-1-yl)ethylamine (138113-09-4)

Conditions	Yield
With ammonia; hydrogen In ethanol; water at 60℃; under 228015 Torr; for 12h; Autoclave;	95%
With hydrogen; ammonium hydroxide; nickel In methanol at 20℃; under 3102.97 Torr; for 20h;	92%
With ammonia; hydrogen In ethanol at 45℃; under 15001.5 Torr; Temperature; Pressure; Green chemistry;	71.2%

(7-methoxy-1-naphthyl)acetonitrile (138113-08-3) → d2-(7-methoxy-naphthalen-1-yl)acetonitrile (1079390-50-3)

Conditions	Yield
With d(4)-methanol; water-d2; potassium carbonate In tetrahydrofuran at 20℃; for 5h;	95%

(7-methoxy-1-naphthyl)acetonitrile (138113-08-3) → 2-(7-methoxynaphthalen-1-yl)acetic acid (6836-22-2)

Conditions	Yield
With water; sodium hydroxide at 120℃; for 0.666667h; Microwave irradiation;	93%

(7-methoxy-1-naphthyl)acetonitrile (138113-08-3) → 2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride (139525-77-2)

Conditions	Yield
With hydrogen; sodium hydroxide In methanol; water at 30℃; under 3000.3 Torr;	92%
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With hydrogen; sodium hydroxide In methanol; water; isopropyl alcohol at 25 - 30℃; under 7500.75 Torr; Stage #2: With hydrogenchloride In methanol; water; isopropyl alcohol at 50 - 55℃; for 1h;	90%
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With ammonia; hydrogen In methanol at 15 - 55℃; under 3750.38 Torr; Autoclave; Stage #2: With hydrogenchloride In methanol; water; ethyl acetate at 0 - 5℃; for 1h;	83%

acetic anhydride (108-24-7) + (7-methoxy-1-naphthyl)acetonitrile (138113-08-3) → agomelatine (138112-76-2)

Conditions	Yield
With hydrogen; Raney nickel In ethanol; water at 70℃; under 22502.3 Torr;	89%
With hydrogen In ethanol; water at 70℃; under 22502.3 Torr;	89%
With hydrogen In ethanol; water at 70℃; under 22502.3 Torr; for 1h;	89%
With hydrogen In ethanol at 60℃; under 37503.8 Torr; for 4h;
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With hydrogen; sodium hydroxide In methanol; water at 30℃; under 3000.3 Torr; Stage #2: acetic anhydride In methanol at 15 - 25℃;

(7-methoxy-1-naphthyl)acetonitrile (138113-08-3) + carbonic acid dimethyl ester (616-38-6) → methyl 2-cyano-2-(7-methoxynaphthalen-1-yl)acetate (148057-30-1)

Conditions	Yield
With sodium at 110℃; for 1h;	88%
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Reflux; Stage #2: carbonic acid dimethyl ester In tetrahydrofuran; mineral oil for 0.5h; Reflux;	80%
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Heating / reflux; Stage #2: carbonic acid dimethyl ester In tetrahydrofuran for 0.5h; Heating / reflux;
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Heating / reflux; Stage #2: carbonic acid dimethyl ester In tetrahydrofuran for 0.5h; Heating / reflux; Stage #3: With hydrogenchloride In water

(7-methoxy-1-naphthyl)acetonitrile (138113-08-3) + methyl iodide (74-88-4) → 2-(7-methoxynaphthalen-1-yl)propionitrile (259866-21-2)

Conditions	Yield
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Metallation; Stage #2: methyl iodide In N,N-dimethyl-formamide for 1h; Methylation;	84%

(7-methoxy-1-naphthyl)acetonitrile (138113-08-3) + diphenyl(vinyl)sulfonium trifluoromethanesulfonate → 1-(7-methoxynaphthalen-1-yl)cyclopropane carbonitrile

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 21℃; for 12h;	83%

carbon dioxide (124-38-9) + (7-methoxy-1-naphthyl)acetonitrile (138113-08-3) → 2-(7-methoxynaphthalen-1-yl)ethanamine carbon dioxide adduct

Conditions	Yield
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With ammonium hydroxide; hydrogen In methanol; water at 40℃; Stage #2: carbon dioxide In toluene at 10 - 15℃;	81%

(7-methoxy-1-naphthyl)acetonitrile (138113-08-3) + methyl iodide (74-88-4) → 2-(7-methoxynaphthalen-1-yl)-2-methylpropanenitrile (1574512-73-4)

Conditions	Yield
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at -30℃; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at -30 - 65℃;	80.3%
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With potassium carbonate In acetone for 0.5h; Reflux; Stage #2: methyl iodide In acetone for 2h; Reflux;	75%

di-tert-butyl dicarbonate (24424-99-5) + (7-methoxy-1-naphthyl)acetonitrile (138113-08-3) → Tert-butyl (2-(7-methoxynaphthalen-1-yl)ethyl)carbamate (1617524-06-7)

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 12h; Inert atmosphere;	80%

bromoacetic acid methyl ester (96-32-2) + (7-methoxy-1-naphthyl)acetonitrile (138113-08-3) → methyl 3-cyano-3-(7-methoxynaphthalen-1-yl)propanoate (259866-37-0)

Conditions	Yield
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With tetrabutylammomium bromide; potassium carbonate In acetone for 0.5h; Reflux; Stage #2: bromoacetic acid methyl ester In acetone for 24h; Reflux;	75%
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With sodium hydride In tetrahydrofuran at 50℃; for 1h; Metallation; Stage #2: bromoacetic acid methyl ester In tetrahydrofuran for 1h; Alkylation; Heating;	67%

(7-methoxy-1-naphthyl)acetonitrile (138113-08-3) + α-bromoacetophenone (70-11-1) → 4-(7-methoxynaphthalen-1-yl)-1-phenylbutane-1,3-dione

Conditions	Yield
Stage #1: (7-methoxy-1-naphthyl)acetonitrile; α-bromoacetophenone With chloro-trimethyl-silane; zinc In tetrahydrofuran for 6h; Blaise Reaction; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 100℃; for 0.5h; pH=2; Blaise Reaction; Inert atmosphere;	75%

Upstream product

• 138113-07-2 2-(2-methoxynaphthalen-8-yl)acetamide 
• 360766-78-5 1-hydroxy-7-methoxy-3,4-dihydro-1-naphthylacetonitrile 
• 59081-65-1 2-(1-hydroxyl-7-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetonitrile 
• 6836-19-7 7-Methoxy-1-tetralone 
• 6836-22-2 2-(7-methoxynaphthalen-1-yl)acetic acid 
• 6836-23-3 (7-methoxy-1-naphthyl)acetic acid chloride 
• 861960-34-1 2-(7-methoxy-3,4-dihydronaphthalen-1-yl)acetonitrile 
• 178366-52-4 1-chloromethyl-7-methoxynaphthalene 
• 6836-21-1 ethyl 2-(7-methoxynaphthalen-1-yl)acetate 
• 27532-26-9 ethyl (1,2,3,4-tetrahydro-7-methoxy-1-naphthyl)acetate 
• 2825-01-6 7-methoxy-1-methylnaphthalene 
• 773837-37-9 sodium cyanide 
• 91571-02-7 1-bromomethyl-7-methoxynaphthalene 
• 1384168-60-8 (7-methoxy-4-oxo-1,2,3,4-tetrahydro-1-naphthyl)acetonitrile 

Downstream Products

• 138113-09-4 2-(7-methoxynaphth-1-yl)ethylamine 
• 138112-79-5 N-[2-(7-methoxy-1-naphthyl)ethyl]propionamide 
• 138112-76-2 agomelatine 
• 138112-82-0 N-[2-(7-methoxynaphth-1-yl)ethyl]-4chlorobutyramide 
• 6836-22-2 2-(7-methoxynaphthalen-1-yl)acetic acid 
• 1595280-04-8 1-(2-(7-methoxynaphthalen-1-yl)ethyl)-3,4-dimethyl-1H-pyrrole-2,5-dione 
• 1595280-22-0 N-(2-(7-methoxynaphthalen-1-yl)ethyl)-4-phenylpiperidine-1-carboxamide 
• 1595280-05-9 1-(2-(7-methoxynaphthalen-1-yl)ethyl)-1H-pyrrole-2,5-dione 
• 1595280-07-1 3,4-dichloro-1-(2-(7-methoxynaphthalen-1-yl)ethyl)-1H-pyrrole-2,5-dione 
• 1385018-58-5 N,N-bis[2-(7-methoxynaphthalen-1-yl)-ethyl]acetamide 
• 1647055-46-6 1-(7-methoxynaphthalen-1-yl)cyclopropane carbonitrile 
• 861960-34-1 2-(7-methoxy-3,4-dihydronaphthalen-1-yl)acetonitrile 
• 138112-95-5 S 20255 
• 138112-91-1 S 20254 

Relevant articles and documents

Method and intermediate for synthesizing 7 - methoxy -1 - naphthalene acetonitrile

The invention relates to the field of organic synthesis, and discloses a preparation method of 7 - methoxy -1 - naphthalene acetonitrile and an intermediate. The method comprises the following steps: (1) reacting 7 - methoxytetrahydro -1 -naphthyl ketone with cyanoacetic acid, (7 - methoxy -3, 4 -dihydro -1 - naphthyl) acetonitrile. (2) (7 - Methoxy -3, 4 - dihydro -1 - naphthyl) acetonitrile was subjected to a halogenation reaction to produce (7 - methoxy -3, 4 - dihydro -4 - halo -1 - naphthyl) acetonitrile. (3) (7 - Methoxy -3, 4 - dihydro -4 - halo -1 - naphthyl) acetonitrile dehalogenated hydrogen to give 7 - methoxy -1 - naphthalene acetonitrile. The method has the advantages of mild reaction conditions, less steps, simple operation and simple and easily available raw materials. There is no need to use harsh conditions, high cost catalysts or high risk chemicals. , As a new method for synthesizing 7 - methoxy -1 - naphthalene acetonitrile, the scheme provided by the invention has a good application prospect.

Preparation method of agomelatine intermediate

The invention relates to a preparation method of an agomelatine intermediate. Specifically, the invention provides a preparation method of an agomelatine important intermediate 2-(7-methoxy-1-naphthyl)acetonitrile II, 7-methoxy-1-tetralone is used as an initial raw material, condensation and oxidation reactions are carried out to obtain the intermediate 2-(7-methoxy-1-naphthyl)acetonitrile, and the preparation method has the advantages of good yield, high product purity, simple reaction and easy operation, and is suitable for industrial production .

The preparation method of the agomelatine intermediate

The invention relates to a preparation method of an agomelatine intermediate. The method specifically comprises the following steps: by using 7-methoxyl tetrahydronaphthalene-1-one and diethyoxyl phosphoryl ethyl acetate as initial raw materials, carrying out condensation, dehydrogenation, ammonolysis and dehydration to obtain the agomelatine intermediate, namely a compound shown in a formula (IV). The preparation method provided by the invention is economical in preparation process and suitable for massively preparing the agomelatine intermediate with high yield.

A compound and its preparation method and application

The invention provides a 1-cyan-1-(7-methoxyl-3, 4-dihdyro-1-naphthyl) methanol ester compound shown as a structural formula I described in the specification, wherein R is H, C1-C6 aliphatic groups or aryl. The invention further provides a preparation method of the compound and an application thereof in preparing agomelatine. The method of synthesizing agomelatine by the 1-cyan-1-(7-methoxyl-3, 4-dihdyro-1-naphthyl) methanol ester compound shown as the structural formula I is mild in condition, lower in production cost, higher in yield and fewer in impurities in end-products of reaction, and is more suitable for industrialized production.

7-methoxy naphthyl acetonitrile synthesis method

The invention discloses a 7-methoxy naphthylacetonitrile synthesis method, which comprises: 1) using 7-methoxy-3,4-dihydro naphthylacetonitrile as a raw material, adopting DDQ as a catalyst, carrying out an oxidation reaction on the 7-methoxy-3,4-dihydro naphthylacetonitrile and introduced oxygen in a halogenated alkane solvent to obtain 7-methoxy naphthylacetonitrile; and 2) extracting the reaction liquid obtained in the step 1), washing, concentrating, and re-crystallizing to obtain the 7-methoxy naphthylacetonitrile. According to the present invention, the 7-methoxy naphthylacetonitrile synthesis method has advantages of low cost, convenient post-treatment and less post-treatment sewage, wherein the by-product is water so as to provide the advantage of green environmental protection.

Method for synthesizing agomelatine important intermediate 7-methoxy naphthylacetonitrile

The invention provides a method for synthesizing an agomelatine important intermediate 7-methoxy naphthylacetonitrile. According to the invention, 7-methoxy-3,4-naphthalene acetonitrile is taken as a raw material, 2,3-dicyano-5,6-dichlorobenzoquinone is taken as a catalyst, and the materials are subjected to an oxidation reaction with oxygen in a halogenated hydrocarbon solvent to obtain the intermediate 7-methoxy naphthylacetonitrile. The method is concise, the production cost is low, the integral yield of the reaction is high, product quality is good, environmental protection is realized, the method is convenient for industrial production, and has large popularization meaning.

Method for preparing important intermediate 7-methoxynaphthyl acetonitrile of Agomelatine

The invention provides a method for preparing an important intermediate 7-methoxynaphthyl acetonitrile of Agomelatine. The method comprises the step of subjecting 7-methoxy-3,4-dihydronaphthyl acetonitrile, which serves as a raw material, to an oxidation reaction with oxygen gas in a haloalkane solvent in the presence of dichlorodicyan benzoquinone which serves as a catalyst, thereby obtaining the intermediate 7-methoxynaphthyl acetonitrile. The method is simple, the production cost is low, the overall yield of reaction is high, the product quality is good, and the method is environmentally friendly, so that the industrial production is facilitated, and the method has a great popularization significance.

Method for synthesizing 7-methoxynaphthalene acetonitrile

The invention provides a method for synthesizing 7-methoxynaphthalene acetonitrile. An intermediate 7-methoxynaphthalene acetonitrile is obtained by carrying out an oxidation reaction of 7-methoxy-3,4-naphthalene acetonitrile serving as a raw material, dichloro-dicyano-benzoquinone serving as a catalyst and oxygen in a halogenated hydrocarbon solvent. The method is simple, low in production cost, high in reaction overall yield, high in product quality, environmentally friendly and convenient in industrialized production, and has great popularization significance.

Preparation method of agomelatine intermediate

The invention discloses a preparation method of an agomelatine intermediate. The preparation method comprises steps as follows: firstly, 1-bromo-7-methoxynaphthalene is dissolved in an organic solvent, and a mixed solution is formed; elementary alkali metal and an initiator are added to a reaction bottle, the organic solvent is added to the reaction bottle and stirred uniformly, the prepared mixed solution is dropwise added slowly, when a reaction liquid is boiled slightly, the organic solvent is supplemented into the reaction bottle and stirring is started, the prepared mixed solution is dropwise added continuously, and a reaction liquid of a 1-bromo-7-methoxynaphthalene Grignard reagent is obtained after the heat preservation reaction; bromoacetonitrile is added to the organic solvent, a bromoacetonitrile mixed liquid is prepared, the prepared bromoacetonitrile mixed liquid is dropwise added slowly to the reaction liquid of the Grignard reagent, and (7-methoxy-1-naphthyl) acetonitrile is obtained after the heat preservation reaction and aftertreatment. With the adoption of the method, industrial production can be realized, 1-bromo-7-methoxynaphthalene is taken as a starting material, the cost can be saved, the product quality is stable, the yield is high, and the preparation method is applicable to large-scale industrial stable production.

Preparation method of 2-(7-methoxyl-1-naphthyl) acetonitrile

The invention discloses a preparation method of 2-(7-methoxyl-1-naphthyl) acetonitrile. 2-(7-methoxyl-1-naphthyl) acetonitrile is prepared through the two steps of a Wittig reaction and an aromatization reaction. The reaction route is short, the overall reaction yield is high, particularly, after a hydrogen acceptor is added in the step2, the obtained product yield is further increased, purity is also high, reaction conditions are mild, no reagent and solvent high in toxicity are involved, and the preparation method is suitable for industrialized production.