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Preparation method of quinoline-5-sulfonyl chloride

A technology of isoquinoline and sulfonyl chloride, applied in the field of medicine and chemical industry, can solve problems such as being unsuitable for industrialized production, cumbersome post-treatment process, polluted environment by waste acid, etc., and achieve the effects of low cost, shortened reaction time, and light environmental pollution

Active Publication Date: 2014-04-16
WUHAN WUYAO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, this method has a long route and cumbersome post-treatment process. The raw materials oleum and thionyl chloride are strong acidic substances, which are expensive and produce a lot of waste acid to pollute the environment, which is not suitable for industrial production.

Method used

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  • Preparation method of quinoline-5-sulfonyl chloride
  • Preparation method of quinoline-5-sulfonyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 38.7g of 5-aminoisoquinoline and 590mL of concentrated hydrochloric acid into a 1000mL reaction flask, cool to below 0°C while stirring, add 100mL of nitrous acid aqueous solution (containing 22g of sodium nitrite) dropwise, and control the temperature at 0°C to 10°C. °C, after the dropwise addition was completed, the reaction was continued for 1 h to obtain a diazotization solution for later use.

[0021] Add 650mL of acetic acid to another 2000mL reaction flask, control the temperature at 10°C to 20°C and let sulfur dioxide flow into it to saturation, then add 80mL of copper chloride solution (containing 8.7g of copper chloride), and then add the above-mentioned diazo solution, after dripping, reacted overnight, extracted with 2×500mL of dichloromethane, washed the organic layer twice, dried, and removed the solvent acetic acid to obtain 42.8g of 5-isoquinolinesulfonyl chloride, yield 70.3%

Embodiment 2

[0023] Add 38.7g of 5-aminoisoquinoline and 590mL of concentrated hydrochloric acid into a 1000mL reaction flask, cool to below -5°C while stirring, add dropwise 100mL of nitrous acid aqueous solution (containing 22g of sodium nitrite), and control the temperature at -5°C ~5°C, after the dropwise addition, continue to keep warm for 1 hour to obtain a diazotization solution for later use.

[0024] Add 650mL of acetic acid to another 2000mL reaction flask, control the temperature at 10°C to 20°C and let sulfur dioxide flow into it to saturation, then add 80mL of copper chloride solution (containing 8.7g of copper chloride), and then add the above-mentioned diazo solution, after dripping, reacted overnight, extracted with 2×500mL of dichloromethane, washed the organic layer twice, dried, and removed the solvent acetic acid to obtain 46.8g of 5-isoquinolinesulfonyl chloride, yield 76.8%

Embodiment 3

[0026] Add 77.4g of 5-aminoisoquinoline and 1180mL of concentrated hydrochloric acid into a 2000mL reaction flask, cool to below -10°C under stirring, add dropwise 200mL of nitrous acid aqueous solution (containing 44g of sodium nitrite), and control the temperature at -10°C ~0°C, after the dropwise addition, continue to keep warm for 1 hour to obtain a diazotization solution for later use.

[0027] Add 1300mL of acetic acid to another 5000mL reaction flask, control the temperature at 10°C to 20°C and feed sulfur dioxide to saturation, then add 160mL of copper chloride solution (containing 17.4g of copper chloride), and then add the above-mentioned diazo After the solution was dropped, reacted overnight, extracted with 2×1000mL of dichloromethane, washed the organic layer twice with water, dried, and removed the solvent acetic acid to obtain 102.1 g of 5-isoquinolinesulfonyl chloride with a yield of 83.7%.

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Abstract

The invention relates to a preparation method of a medical intermediate, quinoline-5-sulfonyl chloride; the preparation method comprises the following steps: taking 5-aminoisquinoline as a raw material and conducting diazo-reaction with sodium nitrite and concentrated hydrochloric acid; conducting a sulfuryl chloridization on the prepared diazotization solution and sulfur dioxide in an acetic acid solvent and obtaining the quinoline-5-sulfonyl chloride; the quinoline-5-sulfonyl chloride can be obtained in one step in the reaction. The preparation method provided by the invention is simple in process and convenient in operation; moreover, the raw material is cheap and can be easily obtained, environmental pollution is light and the yield surpasses 80%, therefore, the preparation method is more suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a preparation method of a medicine intermediate isoquinoline-5-sulfonyl chloride. Background technique [0002] Isoquinoline-5-sulfonyl chloride is a colorless liquid with the chemical formula C 9 h 6 ClNO 2 S, with a molecular weight of 227.7 and a boiling point of 371.2°C, is an important intermediate for the synthesis of Fasudil hydrochloride. Fasudil hydrochloride is a RHO kinase inhibitor. By increasing the activity of myosin light chain phosphatase, dilating blood vessels, reducing the tension of endothelial cells, improving brain microcirculation, and antagonizing inflammatory factors, protecting nerves against apoptosis, Promotes nerve regeneration. [0003] Japanese patents JP11158177, JP11171885, Chinese patent CN102020636A, etc. are still using the traditional synthesis method to synthesize isoquinoline-5-sulfonyl chloride, using isoquinoli...

Claims

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Application Information

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IPC IPC(8): C07D217/02
CPCC07D217/02
Inventor 皮金红丁友友董建强魏金维潘文清谢国范
Owner WUHAN WUYAO PHARMA
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