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Method for synthesizing (7-methoxy-1-naphthyl) acetonitrile

A synthesis method and a methoxyl technology are applied in chemical instruments and methods, preparation of carboxylic acid nitrile, preparation of organic compounds, etc., and can solve the problems of high cost of raw materials, high toxicity of methylene chloride, dark color, etc.

Active Publication Date: 2010-06-09
JIANGSU YUXIANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The operation in this route is relatively cumbersome, and different reaction solvents are used in the two-step reaction. The intermediate product needs to be separated and precipitated. The obtained oily intermediate product has many impurities and dark color, which makes the color and quality of the final product deviate.
The solvent dichloromethane used has high toxicity, low boiling point, poor environmental friendliness and is difficult to recycle
[0012] In summary, there are various defects in the existing synthetic methods, or the yield is low, or the raw materials are not easy to obtain, or the raw materials used are too dangerous to be conducive to industrial production, or the cost of raw materials is relatively expensive, or The disadvantages are cumbersome operation process, high toxicity of solvents, low boiling point, and poor product quality.
The existing technical routes need to be improved in terms of environmental friendliness and cost

Method used

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  • Method for synthesizing (7-methoxy-1-naphthyl) acetonitrile
  • Method for synthesizing (7-methoxy-1-naphthyl) acetonitrile
  • Method for synthesizing (7-methoxy-1-naphthyl) acetonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Dehydration acetonitrile: put 211.2kg of 7-methoxytetralin-1-one, 153.6kg of cyanoacetic acid, 32.4kg of benzylamine, 40kg of heptanoic acid, and 1200kg of toluene into a 3000L reaction kettle. The temperature was raised to 115°C to reflux, and the reflux reaction was divided into water for 24 hours. After cooling, a solution of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile was obtained.

[0027] (2) Dehydroaromatization: 300 kg of DDQ was dissolved in 400 kg of toluene solution, and the solution was added dropwise to the reaction liquid obtained in step (1), the reaction temperature was 25° C., and the reaction was stirred for 2.0 h. The reaction solution was filtered, and the filtrate was washed with alkali, water and saturated brine. After the solvent was removed by distillation under reduced pressure, the residue was recrystallized through ethanol: water (V / V=8: 2) to obtain 222.5kg white to pale yellow crystalline solid (7-methoxy-1-naphthyl) acetonitrile, yi...

Embodiment 2

[0029] (1) Dehydration acetonitrile: Put 176kg of 7-methoxytetralin-1-one, 128kg of cyanoacetic acid, 27kg of benzylamine, 33kg of heptanoic acid, and 1500kg of benzene into a 3000L reaction kettle. The temperature was raised to 86°C to reflux, and the reflux reaction was divided into water for 40 hours. After cooling, a solution of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile was obtained.

[0030] (2) Dehydroaromatization: 250 kg of DDQ was dissolved in 400 kg of benzene solution, and the solution was added dropwise to the reaction solution obtained in step (1), the reaction temperature was 45° C., and the reaction time was 1.0 h. The reaction solution was filtered, and the filtrate was washed with alkali, water and saturated brine. After the solvent was evaporated by distillation under reduced pressure, the residue was recrystallized through ethanol: water (V / V=8: 2) to obtain 177kg of white to light yellow crystalline solid (7-methoxy-1-naphthyl) acetonitrile, yield 90 ...

Embodiment 3

[0032] (1) Dehydration acetonitrile: put 176kg of 7-methoxytetralin-1-one, 102kg of cyanoacetic acid, 21.1kg of benzylamine, 26.4kg of heptanoic acid, and 920kg of toluene into a 2000L reaction kettle. The temperature was raised to 116°C to reflux, and the reflux reaction was divided into water for 30 hours. After cooling, a solution of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile was obtained.

[0033](2) Dehydroaromatization: 227kg of DDQ was dissolved in 230kg of toluene solution, and the solution was added dropwise to the reaction solution obtained in step (1), the reaction temperature was 0°C, and the reaction time was 5h. The reaction solution was filtered, and the filtrate was washed with alkali, water and saturated brine. After the solvent was evaporated by distillation under reduced pressure, the residue was recrystallized from ethanol: water (V / V=8: 2) to obtain 167kg of white to light yellow crystalline solid (7-methoxy-1-naphthyl) acetonitrile, yield 85 %. The...

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Abstract

The invention relates to a method for synthesizing (7-methoxy-1-naphthyl) acetonitrile, which prepares the (7-methoxy-1-naphthyl) acetonitrile by taking 7-methoxy tetralin-1-ketone as a main initial raw material and performing dehydrated acetonitrile synthesis and dehydrogenated aromatization in turn, wherein a single reaction solvent is adopted in the step of a two-step reaction, and the two-step reaction adopts a one-pot process. The synthesis method has mild reaction conditions and simple process operations and has the overall yield of over 94 percent.

Description

technical field [0001] The invention relates to a method for synthesizing (7-methoxyl-1-naphthyl)acetonitrile. Background technique [0002] (7-Methoxy-1-naphthyl)acetonitrile, the CAS number is [138113-08-3], the molecular formula is as follows. [0003] [0004] (7-Methoxy-1-naphthyl)acetonitrile is the key intermediate in the synthesis of agomelatine. Agomelatine (agomelatine), chemical name N-[2-(7-methoxy-1-naphthyl) ethyl] acetamide, trade name Valdoxan, is a melatonin agonist, both Antagonize 5HT 2C , which is the first melatonin-class antidepressant, is effective in treating depression, improving sleep parameters and maintaining sexual function. [0005] (7-Methoxy-1-naphthyl) acetonitrile synthesis method is generally divided into the following categories: [0006] 1.EP0447285 reported the Reformatsky reaction of 7-methoxytetralin-1-one and ethyl bromoacetate, and then prepared (7-methoxy-1-naphthyl)acetic acid by sulfur dehydroaromatization Ethyl ester, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/37C07C253/30
Inventor 张治国肖杨柏
Owner JIANGSU YUXIANG CHEM
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