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Preparation of 2-bromo-4,5-dimethoxy benzenepropanenitrile

A technology of dimethoxyphenylpropionitrile and dimethoxybenzaldehyde, applied in the field of 2-bromo-4, can solve the problems of harsh reaction conditions, long reaction route, low yield and the like, and achieves short reaction route, The effect of simple reaction operation and high yield

Inactive Publication Date: 2009-04-15
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In summary, the above method has disadvantages such as long reaction route, low yield, and harsh reaction conditions, and the cost is relatively high in large-scale production.

Method used

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  • Preparation of 2-bromo-4,5-dimethoxy benzenepropanenitrile
  • Preparation of 2-bromo-4,5-dimethoxy benzenepropanenitrile
  • Preparation of 2-bromo-4,5-dimethoxy benzenepropanenitrile

Examples

Experimental program
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Effect test

Embodiment 1

[0030] (1) 2-bromo-4,5-dimethoxybenzaldehyde

[0031]

[0032] Add 100g (0.602mol) of 3,4-dimethoxybenzaldehyde and 400ml of glacial acetic acid into the reaction flask together, stir at room temperature to dissolve, slowly add 30.8ml of bromine (0.602mol) dropwise, at 20-30°C After reacting for 6 hours, 200ml of water was added to precipitate a yellow solid, which was filtered by suction, washed with water, and dried in vacuo to obtain 127.6g of white crystals of 2-bromo-4,5-dimethoxybenzaldehyde, yield 86.5%, mp: 151 ~152°C.

[0033] (2) 2-bromo-4,5-dimethoxycinnamonitrile

[0034]

[0035] Dissolve 127.6 g (0.52 mol) of 2-bromo-4,5-dimethoxybenzaldehyde in 400 ml of tetrahydrofuran and 200 ml of acetonitrile, raise the temperature to reflux, add 35 g (0.62 mol) of potassium hydroxide in batches, reflux for 10 hours, and the reaction is complete , evaporated the reaction solvent, added 200ml of water, extracted twice with ethyl acetate, anhydrous MgSO 4 Dry, distill...

Embodiment 2

[0050] (1) 2-bromo-4,5-dimethoxycinnamonitrile

[0051] Dissolve 122.0 g (0.50 mol) of 2-bromo-4,5-dimethoxybenzaldehyde in 600 ml of acetonitrile, heat up to reflux, add 24.0 g (0.60 mol) of sodium hydroxide in batches, and react at reflux for 10 hours. Add 100ml of acetonitrile, concentrate after the reaction, add 200ml of water, extract twice with ethyl acetate, anhydrous MgSO 4 After drying, the solvent was evaporated and recovered, and recrystallized from ethanol to obtain 91.4 g of 2-bromo-4,5-dimethoxycinnamonitrile, with a yield of 68.5%, and mp: 147-148°C.

[0052] (2) 2-Bromo-4,5-dimethoxyphenylpropionitrile

[0053] Dissolve 120.0g (0.45mol) of 2-bromo-4,5-dimethoxycinnamonitrile in 100ml of pyridine and 400ml of methanol, add 48.6g (0.90mol) of potassium borohydride in batches, and slowly raise the temperature and reflux for 24 hours , after the reaction was completed and cooled, the unreacted potassium borohydride was decomposed with 10% hydrochloric acid, extra...

Embodiment 3

[0055] (1) 2-bromo-4,5-dimethoxyphenylpropionitrile

[0056] Dissolve 120.0 g (0.45 mol) of 2-bromo-4,5-dimethoxycinnamonitrile in 800 ml of methanol, add 20 g of 10% palladium carbon in batches, and pass through hydrogen for reduction reaction for 12 hours. After the reaction is complete, filter off Palladium carbon, the solvent was distilled off and recovered, and recrystallized from ethanol to obtain 102.4 g of 2-bromo-4,5-dimethoxyphenylpropionitrile as white crystals, with a yield of 84.6%, mp: 76-78°C.

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Abstract

The invention relates to a method for preparing 2-bromine-4, 5-dimethoxy benzene propane nitrile, which consists of steps: 3-4-dimethoxy benzaldehyde and bromine are dissolved in acetic acid to be reacted; when solid is precipitated, 2-bromine-4, 5-dimethoxy benzaldehyde crystal is obtained through suction filtration; the crystal and acetonitrile are dissolved in organic solvent; after a catalytic reaction, yellow solid is precipitated, cooled, extracted and dried to get 2-bromine-4, 5-dimethoxy cinnamonitrile solid which is then dissolved in methanol with reducing agent and is reduced to obtain 2-bromine-4, 5-dimethoxy benzene propane nitrile after a reflux reaction; or the obtained 2-bromine-4, 5-dimethoxy cinnamonitrile is reduced with hydrogen under the catalysis of palladium-charcoal to get 2-bromine-4, 5-dimethoxy benzene propane nitrile. The 2-bromine-4, 5-dimethoxy benzene propane nitrile prepared by the invention has high yield coefficient; original raw materials of the preparation method are easy to get; the price is low; the reaction operation is simple; the reaction route is short; and the method is easy for industrialization production.

Description

technical field [0001] The invention belongs to the field of preparation of phenylpropionitrile, in particular to a preparation method of 2-bromo-4,5-dimethoxybenzonitrile. Background technique [0002] In recent years, with the acceleration of people's life and work rhythm and the aging of society, the incidence of cardiovascular and cerebrovascular diseases is gradually increasing. Myocardial ischemic diseases such as angina pectoris and myocardial infarction are a kind of heart disease with high incidence. Cerebrovascular disease is the main cause of death. According to incomplete statistics, the incidence of myocardial ischemic disease is about 6% in middle-aged and elderly people, and anti-myocardial ischemic drugs have always been one of the research hotspots of new drugs (Pharmacol.Res.2006, 53 (5): 440~ 445). [0003] The new anti-myocardial ischemia drug Ivabradine (Ivabradine) was developed by the French company Servier and was approved for marketing in Europe in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/37C07C253/30
Inventor 赵圣印梁红玉邵志宇陈睿
Owner DONGHUA UNIV
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