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Preparation method of chlorquinaldol

A technology of chloroquinadol and methyl quinoline, applied in the field of drug synthesis, can solve the problems of large amount of sodium hypochlorite solution, increase the cost of treating waste liquid, reduce yield and the like, meet the requirements of reaction equipment, and reduce waste liquid. Generate, improve quality and yield effects

Active Publication Date: 2021-10-22
北京斯利安药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] This process eliminates the pollution of chlorine gas, but still uses highly volatile hydrochloric acid, and the amount of sodium hypochlorite solution is large, which will dissolve part of the generated products during the reaction process, resulting in a decrease in yield, and more waste liquids, increasing cost of waste disposal

Method used

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  • Preparation method of chlorquinaldol
  • Preparation method of chlorquinaldol
  • Preparation method of chlorquinaldol

Examples

Experimental program
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Effect test

Embodiment 1

[0067] Put 10g of 8-hydroxy-2-methylquinoline, 50mL of dichloromethane and 0.35g of aluminum chloride into a 250mL reaction bottle, stir and cool down to 20~30℃, add 14.2g of tert-butyl hypochlorite, 32~41 ℃ insulation reaction for 7h.

[0068] Cool the reaction solution to 20-30°C, filter, add 15mL of concentrated hydrochloric acid dropwise into the filtrate, precipitate out, filter, add 150mL of water, stir to dissolve, slowly add ammonia water until the pH is 3.0, precipitate solid, filter, rinse, Dried rough.

[0069] The crude product was refined with 160 mL of absolute ethanol and 20 mL of water to obtain 9.1 g of pure chloroquinaldol, with a yield of 63.28% and a HPLC purity of 99.58%.

Embodiment 2

[0071] Put 20g of 8-hydroxy-2-methylquinoline, 200mL of chloroform and 1.0g of aluminum chloride into a 500mL reaction bottle, stir and cool down to 20-30°C, add 28.0g of tert-butyl hypochlorite, and keep warm at 32-41°C Reaction 8h.

[0072] Cool the reaction solution to 20-30°C, filter, add 20mL of concentrated hydrochloric acid dropwise to the filtrate, precipitate out, filter, add 200mL of water, stir to dissolve, slowly add ammonia water until the pH is 3.5, precipitate solid, filter, rinse, Dried rough.

[0073] The crude product was refined with 280 mL of absolute ethanol and 30 mL of water to obtain 19.7 g of pure chloroquinaldol, with a yield of 68.86% and a HPLC purity of 99.65%.

Embodiment 3

[0075] Put 10g of 8-hydroxy-2-methylquinoline, 80mL of dichloromethane and 0.5g of aluminum chloride into a 250mL reaction bottle, stir and cool down to 20-30°C, add 14g of tert-butyl hypochlorite, 32-41°C Insulation reaction 9h.

[0076] Cool the reaction solution to 20-30°C, filter, add 12mL of concentrated hydrochloric acid dropwise into the filtrate, precipitate out, filter, add 100mL of water, stir to dissolve, slowly add ammonia water until the pH is 4.0, precipitate solid, filter, rinse, Dried rough.

[0077] The crude product was refined with 100 mL of acetonitrile and 10 mL of water to obtain 9.5 g of pure chloroquinaldol, with a yield of 66.05% and an HPLC purity of 99.70%.

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Abstract

The invention provides a preparation method of chloroquinaldoll. The preparation method comprises the following step: in the presence of a catalyst Lewis acid, carrying out a reaction I on a material containing 8-hydroxy-2-methylquinoline and tert-butyl hypochlorite to obtain the chloroquinaldol. According to the method, the tert-butyl hypochlorite is used for replacing chlorine to serve as a reaction raw material, so good selectivity is achieved, byproducts are few, reaction operability is strong, light shielding and gas protection are not needed, quality and yield are improved, the purity of chlorquinaldol is 99.00% or more, and the quality of chlorquinaldol is ensured. In the reaction process, generation of waste liquid is reduced, pollution to the environment is avoided to the maximum extent, cost is saved, quality is improved, and the method is an environment-friendly process suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of chloroquinaldol. Background technique [0002] Chlorquinaldol is a broad-spectrum bacteriostatic agent with the following structure: [0003] [0004] The chemical name is: 5,7-dichloro-8-hydroxy-2-methylquinoline, the molecular weight is 228.07, it is a yellow needle-like crystal with a slightly pungent smell, and it has antifungal, trichomonas, bacteria (G+ and G-), antimicrobial pathogen activity such as chlamydia and mycoplasma. Because it is slightly soluble in water, pathogenic microorganisms generally enter the pathogenic cells through endocytosis, which changes the pH value of the pathogenic cells, inhibits the metabolism of the pathogens, and eventually leads to the death of the pathogens, while human epithelial cells have no phagocytosis function for chloroquinaldol, so the When the medicine is used externally, it has less adverse rea...

Claims

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Application Information

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IPC IPC(8): C07D215/28
CPCC07D215/28
Inventor 阮长浩廖俊凯张书彬郑莎易斌
Owner 北京斯利安药业有限公司
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