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Synthetic method for 7-methoxy-1-naphthylacetonitrile

A synthetic method and methoxyl technology, applied in the field of new process for the preparation of acetonitrile, can solve the problems of expensive raw materials, difficult acquisition of raw materials, cumbersome operation process, etc., and achieve shortened reaction time, good catalytic effect and reaction selectivity, and simplified The effect of the process operation step

Active Publication Date: 2014-12-24
JIANGSU YUXIANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] 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.
Existing technical routes need to be improved in terms of environmental friendliness and cost

Method used

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  • Synthetic method for 7-methoxy-1-naphthylacetonitrile
  • Synthetic method for 7-methoxy-1-naphthylacetonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Dehydration acetonitrile: put 100 kg of 7-methoxytetralin-1-one, 100 kg of cyanoacetic acid, 10 kg of benzylamine, and 600 kg of toluene into a 1000L reaction kettle. The temperature was raised to 116°C to reflux, and the reflux reaction was divided into water for 8 hours. After cooling, a solution of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile was obtained.

[0031] (2) Dehydroaromatization: 150 kg of DDQ was dissolved in 200 kg of toluene solution, and the solution was added dropwise to the reaction liquid obtained in step (1), the reaction temperature was 50° C., and the reaction was stirred for 0.5 h. The reaction solution was filtered, and the filtrate was washed with alkali and saturated brine. After the solvent was removed by distillation under reduced pressure, the residue was recrystallized from ethanol: water (V / V=7:3) to obtain 108.5 kg of white to pale yellow crystalline solid (7-methoxy-1-naphthyl) acetonitrile, yield 97%. The measured melting poi...

Embodiment 2

[0033] (1) Dehydration acetonitrile: put 200kg of 7-methoxytetralin-1-one, 150kg of cyanoacetic acid, 10kg of benzylamine, 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 20 hours. After cooling, a solution of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile was obtained.

[0034] (2) Dehydroaromatization: 270 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 30° C., and the reaction time was 2.0 h. The reaction solution was filtered, and the filtrate was washed with alkali and saturated brine. After removing the solvent by distillation under reduced pressure, the residue was recrystallized from ethanol:water (V / V=5:5) to obtain 208kg of white to light yellow crystalline solid (7-methoxy-1-naphthyl)acetonitrile, yield 93 %. The measured melting point is 82.5-83.4°...

Embodiment 3

[0036] (1) Dehydration acetonitrile: Put 250kg of 7-methoxytetralin-1-one, 300kg of cyanoacetic acid, 75kg of benzylamine, and 2000kg 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 3 hours. After cooling, a solution of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile was obtained.

[0037] (2) Dehydroaromatization: 350kg of DDQ was dissolved in 550kg of toluene solution, and the solution was added dropwise to the reaction solution obtained in step (1), the reaction temperature was 80°C, and the reaction time was 0.5h. The reaction solution was filtered, and the filtrate was washed with alkali and saturated brine. After the solvent was removed by distillation under reduced pressure, the residue was recrystallized from ethanol:water (V / V=3:7) to obtain 251kg of white to pale yellow crystalline solid (7-methoxy-1-naphthyl)acetonitrile, yield 90 %. Determination of melting point 81-83 ℃....

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Abstract

The invention discloses a synthetic method for 7-methoxy-1-naphthylacetonitrile. By means of the method, 7-methoxy-1-tetralone is taken as the main starting material and subjected to a dehydration cyanation reaction and a dehydrogenation aromatization reaction sequentially for preparation, wherein the dehydration cyanation adopts single amine catalyst; the same reaction solvent is adopted in the dehydration cyanation reaction and the dehydrogenation aromatization reaction, a one-pot method reaction process is adopted for direct preparation, an intermediate product of the dehydration cyanation reaction is not required to be subjected to separation and purification treatment, and a produced solution of the dehydration cyanation reaction is directly applied to the dehydrogenation aromatization reaction. The final product yield is increased and the product quality is improved by increasing the reaction temperature and optimizing the technical conditions; and the synthetic method has the advantages that the reaction conditions is mild, the technical operation is simple and convenient, and the total yield can reach 97%.

Description

technical field [0001] The invention relates to a chemical preparation method, in particular to a new preparation process of (7-methoxy-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] Synthetic Communications (31(4), 621-629; 2001) reported that 7-methoxytetrahydronaphthalene-1-one was used as a raw material, which was first sub...

Claims

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Application Information

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IPC IPC(8): C07C255/37C07C253/30
Inventor 张治国肖杨柏程红伟李清龙
Owner JIANGSU YUXIANG CHEM