Method for preparing 2,4-dyhydroxy-6-methylnicotinate

A technology of ethyl methylnicotinate and diethylmalonate, applied in the field of preparation of ethyl 2,4-dihydroxy-6-methylnicotinate, can solve unfavorable industrial production, low yield, production High cost and other issues, to achieve the effect of green reaction system, simple preparation method, and less harsh reaction conditions

Inactive Publication Date: 2017-01-04
CHENGDU BAISHIXING SCI & TECH IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After searching, the ring-closing reaction mentioned in the existing synthetic method needs to be carried out at a high temperature of 140-150°C, and the yield is lower than 80%. The production cost is high, and the required production equipment is special, which is not conducive to industrial production

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  • Method for preparing 2,4-dyhydroxy-6-methylnicotinate
  • Method for preparing 2,4-dyhydroxy-6-methylnicotinate

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Embodiment 1

[0014] A preparation method of ethyl 2,4-dihydroxy-6-methylnicotinate, ethyl 3-aminocrotonate and diethyl malonate successively undergo Claisen ester condensation and condensation under the action of sodium ethoxide Dickermann ester condensation reaction, after the reaction is over, cool the reaction system to 50°C, concentrate under reduced pressure, add basic activated carbon to the concentrated solution, filter, cool the filtrate to below 0°C, adjust the pH of the filtrate with ammonium chloride value to 2, the resulting solid was dried at a temperature of 50°C to obtain ethyl 2,4-dihydroxy-6-methylnicotinate. The temperature of the reaction is 80°C, the reaction time is 20h, the system solvent is absolute ethanol, and the weight ratio of ethyl 3-aminocrotonate, diethyl malonate and sodium ethylate is 0.8:1.5:1 .

Embodiment 2

[0016] A preparation method of ethyl 2,4-dihydroxy-6-methylnicotinate, ethyl 3-aminocrotonate and diethyl malonate successively undergo Claisen ester condensation and condensation under the action of sodium ethoxide Dickermann ester condensation reaction, after the reaction is over, cool the reaction system to 60°C, concentrate under reduced pressure, add basic activated carbon to the concentrated solution, filter, cool the filtrate to below 0°C, adjust the pH of the filtrate with ammonium chloride value to 3, the resulting solid was dried at a temperature of 60° C. to obtain ethyl 2,4-dihydroxy-6-methylnicotinate. The temperature of the reaction is 90°C, the reaction time is 30h, the system solvent is absolute ethanol, and the weight ratio of ethyl 3-aminocrotonate, diethyl malonate and sodium ethylate is 1.5:2.5:1 .

Embodiment 3

[0018] A preparation method of ethyl 2,4-dihydroxy-6-methylnicotinate, ethyl 3-aminocrotonate and diethyl malonate successively undergo Claisen ester condensation and condensation under the action of sodium ethoxide Dickermann ester condensation reaction, after the reaction is over, cool the reaction system to 53°C, concentrate under reduced pressure, add basic activated carbon to the concentrated solution, filter, cool the filtrate to below 0°C, adjust the pH of the filtrate with ammonium chloride value to 2.4, the resulting solid was dried at a temperature of 54°C to obtain ethyl 2,4-dihydroxy-6-methylnicotinate. The temperature of the reaction is 83°C, the reaction time is 24h, the system solvent is absolute ethanol, and the weight ratio of ethyl 3-aminocrotonate, diethyl malonate and sodium ethylate is 1:1.8:1 .

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Abstract

The invention discloses a method for preparing 2,4-dyhydroxy-6-methylnicotinate. The method comprises the following steps: performing a Claisen ester condensation reaction and a Dieckmann condensation reaction on ethyl 3-aminocrotonate and diethyl malonate under the action of sodium ethoxide in sequence, thereby generating a product 2,4-dyhydroxy-6-methylnicotinate. The two steps of reactions, namely, the Claisen ester condensation reaction and the Dieckmann condensation reaction, of the method disclosed by the invention are both performed in one system, so that the reaction time is remarkably shortened, the production cost is greatly lowered, the method is simple, the reaction system is green and environmental-friendly, reaction conditions are not rigorous, the purity of a prepared product is 99% or greater, the yield of the product can be up to 80% or greater, and thus the method is applicable to industrial large-scale production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of ethyl 2,4-dihydroxy-6-methylnicotinate. Background technique [0002] 2,4-dihydroxy-6-methylnicotinic acid ethyl ester, English name: 3-Pyridinecarboxylic acid, 1,6-dihydro-4-hydroxy-6-oxo-, ethyl ester, molecular formula: C 7 h 7 NO 4 , molecular weight 169.1348, density: 1.555g / cm 3 , melting point: 205°C, boiling point: 363.155°C at 760mmHg, flash point: 173.43°C, vapor pressure: 0mmHg at 25°C, CAS: 70254-52-3, molecular structure formula is: [0003] Ethyl 2,4-dihydroxy-6-methylnicotinate is an important organic chemical intermediate, which has broad application prospects in the fields of medicine, dyes and pesticides. Its derivatives are mainly used in the synthesis of cardiovascular diseases, new nervous system drugs and anticancer drugs in the field of medicine. Therefore, the synthesis of ethyl 2,4-dihydroxy-6-methylnic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/80C07D213/803
CPCC07D213/80C07D213/803
Inventor 袁汉
Owner CHENGDU BAISHIXING SCI & TECH IND
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