Synthesis method of cyclopropanecarboxylic acid

A synthetic method, the technology of cyclopropanecarboxylic acid, applied in the direction of organic chemistry, etc., can solve the problem of difficult disposal of waste salt, and achieve the effect of less three wastes, easy control, and mild reaction conditions

Active Publication Date: 2022-01-11
SHANDONG GUOBANG PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that highly toxic dimethyl sulfate needs to be used, and a large amount of waste salt will be produced after the reaction is completed, which is difficult to handle

Method used

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  • Synthesis method of cyclopropanecarboxylic acid
  • Synthesis method of cyclopropanecarboxylic acid
  • Synthesis method of cyclopropanecarboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Add 160.00 g of 2,4-dichloro-5-fluoro-acetophenone, 320.00 g of toluene, and 50.10 g of sodium methoxide (1.2 equivalents) in sequence in a 500 ml reactor, seal the reactor, replace the system with nitrogen three times, and then introduce carbon monoxide until the pressure is 3.8MPa, then raise the temperature to 45°C, at this time, the pressure inside the reactor is 4.5MPa, control the reaction temperature at 50°C, keep the pressure inside the reactor at 4.5MPa, keep the temperature for 5 hours, then the reaction is over, then cool down to 25°C Afterwards, the kettle was opened to obtain the toluene suspension of Intermediate 1. The quality of intermediate 1 in the external standard calculation suspension is 168.84g, and the yield is 85%.

Embodiment 2

[0055] The difference between the method of this example and Example 1 is that the reaction temperature is 55° C., and other steps are the same. The mass of intermediate 1 in the suspension calculated by external standard is 188.70 g, and the yield is 95%.

Embodiment 3

[0057] The difference between the method of this example and Example 1 is that the reaction temperature is 60°C, other steps are the same, the mass of intermediate 1 in the suspension calculated by external standard is 176.78g, and the yield is 89%.

[0058] Embodiment 1 to embodiment 3 experiment summary :

[0059] It can be seen from Examples 1-3 that when the temperature is changed within the range of 45-60°C, the yield of intermediate 1 increases first and then decreases as the temperature increases, so it is determined that the temperature of the present invention is best controlled at 55°C .

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Abstract

The invention discloses a synthesis method of cyclopropanecarboxylic acid. The synthesis method comprises the following steps: with 2,4-dichloro-5-fluoro-acetophenone and carbon monoxide as raw materials, generating sodium beta-2,4-dichloro-5-fluoro-benzoylvinyl alcoholate under the action of sodium methoxide at high pressure, then carrying out amination via cyclopropylamine salt, and successively carrying out reactions such as cyclization, beta-keto acid esterification, hydrolysis and the like to prepare cyclopropanecarboxylic acid. According to the invention, synthesis raw materials are easy to obtain, a synthesis process is simple, reaction conditions are mild, production cost is reduced, production safety is ensured, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and also belongs to the technical field of synthesis of pharmaceutical raw materials, in particular to a synthesis method of cyclopropanecarboxylic acid. Background technique [0002] Quinolones and azaquinolones are well known antimicrobial agents which are known by various names such as nalidixic acid, ciprofloxacin, ofloxacin, norfloxacin, lomefloxacin, enoxacin, sparxacin Star, pefloxacin, etc. have been commercially available for more than 20 years. The main use of these agents is to treat bacterial infections. Gellert et al. synthesized the first quinolone compound in 1976 and discovered its mechanism of action in 1976. The bactericidal properties of quinolones and azaquinolones are due to their potent inhibition of bacterial DNA gyrase, which regulates supercoiling, uncoiling, and spatial geometry of bacterial DNA functions that control DNA replication and repair, Requ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/56
CPCC07D215/56
Inventor 邱正洲李琦斌肖兵张小垒于童
Owner SHANDONG GUOBANG PHARMA
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