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A kind of 2-bromo-4,5-dimethoxycinnamonitrile and preparation method thereof
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A technology of dimethoxymeat and dimethoxybenzaldehyde, applied in the field of 2-bromo-4, can solve the problems of harsh reaction conditions, long reaction route and high cost, and achieves short reaction route, simple reaction operation, Inexpensive effect
Inactive Publication Date: 2011-12-14
DONGHUA UNIV
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[0008] In summary, the above method has the disadvantages of long reaction route, low yield, harsh reaction conditions, etc., and the cost is relatively high in large-scale production.
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Embodiment 1
[0034] (1) 2-bromo-4,5-dimethoxybenzaldehyde
[0035]
[0036] Add 100g (0.602mol) of 3,4-dimethoxybenzaldehyde and 400ml of glacial acetic acid into the reaction flask, stir at room temperature to dissolve them, 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.
[0037] (2) 2-bromo-4,5-dimethoxycinnamonitrile
[0038]
[0039] 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, evaporate a...
Embodiment 2
[0044] (1) 2-bromo-4,5-dimethoxycinnamonitrile
[0045] 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 Dry, evaporate and recover the solvent, recrystallize from ethanol to obtain 91.4 g of 2-bromo-4,5-dimethoxycinnamonitrile, yield 68.5%, mp: 147-149°C.
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Abstract
The present invention relates to a kind of 2-bromo-4,5-dimethoxycinnamonitrile compound, and its structural formula is: Its preparation comprises: (1) 3,4-dimethoxybenzaldehyde and bromine molar ratio 1 : 1~2, take acetic acid as reaction solvent and react at 0~110 ℃ for 1~24 hours, add water to cool, get 2-bromo-4,5-dimethoxybenzaldehyde white crystals by suction filtration; (2) 2 -Bromo-4,5-dimethoxybenzaldehyde and acetonitrile are dissolved in an organic solvent at a ratio of 1 gram: 1 to 100 milliliters, under the action of a basic catalyst, reflux reaction for 1 to 48 hours, cooling and adding water , extracted, dried, and evaporated to obtain 2-bromo-4,5-dimethoxycinnamonitrile brownish white to light yellow crystalline solid. The yield of 2-bromo-4,5-dimethoxycinnamonitrile prepared by the invention is high, the starting material of the preparation method is easy to obtain, the price is cheap, the reaction operation is simple, the reaction route is short, and the industrial production is easy.
Description
technical field [0001] The invention belongs to the field of cinnamonitrile and its preparation, in particular to 2-bromo-4,5-dimethoxycinnamonitrile and its preparation method. 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 Euro...
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