Method for preparing 1,4-dihydropyridine by taking acidic ionic liquid as catalyst

A technology of acidic ionic liquid and dihydropyridine, which is applied in chemical recovery, organic chemistry, etc., can solve the problems of production equipment corrosion, increase the inconvenience of process operation, etc., and achieve the effects of reducing pollution, easy operation, and cost reduction

Inactive Publication Date: 2013-04-17
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method can obtain 1,4-dihydropyridine in a good yield, the irritation and volatility of acet

Method used

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  • Method for preparing 1,4-dihydropyridine by taking acidic ionic liquid as catalyst
  • Method for preparing 1,4-dihydropyridine by taking acidic ionic liquid as catalyst
  • Method for preparing 1,4-dihydropyridine by taking acidic ionic liquid as catalyst

Examples

Experimental program
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Embodiment 1

[0030] Ammonium acetate (7.7g, 100mmol), methyl propiolate (16.8g, 200mmol) and benzaldehyde (10.6g, 100mmol) were thoroughly mixed, and 1-acetic acid-3-methylimidazolium chloride (1.1g) was used as a catalyst , reacted at 50° C. for 1.0 hour, cooled, poured into 30 ml of ice water, filtered with suction, washed, and dried to obtain 25.5 g of the product, with a yield of 93.5%.

Embodiment 2

[0032] Ammonium bicarbonate (7.9g, 100mmol), methyl propiolate (25.2g, 300mmol) and p-tolualdehyde (12.0g, 100mmol) were thoroughly mixed, and 1-acetic acid-3-methylimidazolium bromide (2.4 g) as a catalyst, reacted at 80°C for 0.5 hours, cooled, poured into 100 ml of ice water, filtered with suction, washed, and dried to obtain 25.6 g of the product with a yield of 89.2%.

Embodiment 3

[0034] Ammonium bicarbonate (7.9g, 100mmol), methyl propiolate (16.8g, 200mmol) and m-methoxybenzaldehyde (13.6g, 100mmol) were thoroughly mixed, and 1-acetic acid-3-methylimidazolium bromide ( 0.7 g) was used as a catalyst, reacted at 70° C. for 1.0 hour, cooled, poured into 150 ml of ice water, filtered with suction, washed, and dried to obtain 27.5 g of the product with a yield of 91.0%.

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Abstract

The invention discloses a method for preparing 1,4-dihydropyridine by taking an acidic ionic liquid as a catalyst, comprising the following steps of: taking an amine compound shown in formula (I), a propiolate compound shown in formula (II) and a benzaldehyde compound shown in formula (III) as raw materials in a solvent-free condition, wherein the ratio of the amounts of substance of the raw materials is 1: (2 to 4): 1; reacting for 0.5 to 2 hours at a reaction temperature of 50-100 DEG C under the catalysis of the acidic ionic liquid; and performing separation treatment on the reaction solution to obtain the 1,4-dihydropyridine shown in formula (IV). According to the method, no solvent is used during the preparation process, thus simplifying operation process and reducing cost; the used catalyst is the acidic ionic liquid and capable of being cyclically used, and the technical process is environment-friendly; and the method is moderate in reaction conditions, simple and convenient to operate, easy to separate products, good in product quality and high in yield.

Description

technical field [0001] The invention relates to a method for preparing 1,4-dihydropyridine, in particular to a method for preparing 1,4-dihydropyridine under solvent-free conditions by using benzaldehyde, propiolate and amine compounds as raw materials and using acidic ionic liquid as a catalyst. - The method of dihydropyridine. Background technique [0002] 1,4-Dihydropyridine is an important heterocyclic compound, which has good physiological activity and is widely used in biology and medicine. At present, it has been clinically used for neuroprotection, anti-platelet aggregation, vasodilation, diabetes, anti-brain atrophy agent for Parkinson's disease, chemotherapy agent for tumor treatment, anti-hypertension, angina pectoris, etc. In view of its many significant pharmacological activities, the research on 1,4-dihydropyridine has attracted the attention of researchers at home and abroad. [0003] 1,4-Dihydropyridine is usually prepared by the Hantzsch method, that is, a...

Claims

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Application Information

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IPC IPC(8): C07D211/90
CPCY02P20/584
Inventor 何敬宇刘斯婕杨凯王晓霞高翔师维康安文墨田竞超
Owner SHIJIAZHUANG UNIVERSITY
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