Water phase clean synthesis method of 1,4-dihydropyridine compounds

A technology of dihydropyridine and compounds, applied in the field of aqueous phase clean synthesis 1, can solve the problems of easy volatilization of ammonia water, environmental pollution, waste of raw materials, etc., and achieve the effects of easy industrial scale-up, wide source of raw materials, energy saving and emission reduction

Inactive Publication Date: 2011-09-07
YANCHENG TEACHERS UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Organic solvent as a reaction medium is not only costly but also causes environmental pollution, and it is difficult to dispose of solvent-free reaction products after agglomeration; the cost of organic ammonium salt is high, ammonia water is volatile and polluted, and the decomposition temperature of ammonium carbonate is low at 50-60 °C. Decompose continuously during the process, so the amount of ammonium salt is generally 3-4 times that of aromatic aldehyde, and the decomposed carbon dioxide, ammonia, and water are cooled into ammonium carbonate agglomerates in the condenser tube, which is easy to cause blockage of the condenser tube, not only wasting a lot of raw materials , which brings difficulties to the post-processing

Method used

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  • Water phase clean synthesis method of 1,4-dihydropyridine compounds
  • Water phase clean synthesis method of 1,4-dihydropyridine compounds
  • Water phase clean synthesis method of 1,4-dihydropyridine compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0020] In a 10mL round bottom flask, add 5mmol (0.53g) of benzaldehyde, 10mmol (1.30g) of ethyl acetoacetate, 5mmol (0.48g) of ammonium carbonate and 5ml of water, and seal the bottle mouth with a glass stopper or rubber stopper to seal the reaction system . Stir at 60°C for 2 hours, cool and filter, and recrystallize from 95% ethanol to obtain 4-phenyl 1,4-dihydropyridine product with a yield of 85%.

Embodiment 2

[0022] In a 25mL round bottom flask, add 5mmol (0.76g) of 2-nitrobenzaldehyde, 10mmol (1.30g) of ethyl acetoacetate, 5mmol (0.48g) of ammonium carbonate and 20ml of water, and stopper the bottle with a glass or rubber stopper Mouth closed reaction system. Stir at 60°C for 2 hours, cool and filter, and recrystallize from 95% ethanol to obtain 4-(2-nitro)phenyl 1,4-dihydropyridine product (nifedipine), with a yield of 86%.

Embodiment 3

[0024] In a 25mL round bottom flask, add 5mmol (0.76g) of 2-nitrobenzaldehyde, 10mmol (1.16g) of methyl acetoacetate, 7.5mmol (0.72g) of ammonium carbonate and 20ml of water, and stopper with a glass or rubber stopper Seal the reaction system at the mouth of the bottle. Mix and stir at 60°C for 2 hours, cool and filter, and recrystallize from 95% ethanol to obtain 4-(2-nitro)phenyl 1,4-dihydropyridine product with a yield of 86%.

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Abstract

The invention discloses a water phase clean synthesis method of 1,4-dihydropyridine compounds. The method is as follows: aromatic aldehyde, acetoacetate and ammonium carbonate or ammonium bicarbonate are used as raw materials, no catalyst is added, water is used as the reaction medium to replace organic solvent, the raw materials are heated and stirred in a sealed system to react and synthesize the target compounds. Compared with the prior art, the method has the following advantages: (1) the raw material sources are available, the preparation method is convenient; particularly, compared withorganic ammonium salts such as ammonium formate and ammonium acetate, ammonium carbonate or ammonium bicarbonate used as the source of nitrogen atoms, the cost is low and the material is non-toxic and non-corrosive; (2) water is used as the reaction medium in the synthesis process, the reaction in the sealed system is safe and smooth can easily be industrialized and is an environmentally friendlychemical process; and (3) the reaction does not use catalyst and organic solvent, the operation process is simplified and the effects of energy saving and emission reduction are obvious.

Description

A technical field [0001] The invention relates to a method for cleanly synthesizing 1,4-dihydropyridine compounds in an aqueous phase, and belongs to the technical field of chemical material preparation. The method is applicable to the occasions where aromatic aldehydes, acetoacetates, and inorganic ammonium salts are used as raw materials, water is used instead of organic solvents as reaction media, and the target compound is realized by heat preservation and stirring reaction in a closed system. Two background technology [0002] 1,4-Dihydropyridine compounds have a wide range of biological functions and are widely used in biology and medicine. For example, the representative compound nifedipine, as the first-generation calcium antagonist, is especially suitable for angina pectoris caused by coronary artery spasm, and was one of the best-selling drugs in the world in the mid-1980s. In addition, such compounds are used for the treatment of diseases such as angina pectoris,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/02C07D211/90
Inventor 方东缪小翠赵静王鹏
Owner YANCHENG TEACHERS UNIV
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