Supercharge Your Innovation With Domain-Expert AI Agents!

Method for synthesizing 2-chloronicotinic acid by one-step oxidation

A technology of oxidative synthesis and chloronicotinic acid, applied in the direction of organic chemistry, can solve the problems of high cost, high price of oxidant, unsuitable for large-scale industrial production, etc., and achieve the effect of low cost and high purity

Active Publication Date: 2014-06-11
NANJING REDSUN BIOCHEM CO LTD +1
View PDF9 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] (1) Niacin is used as the starting material for N-oxidation with hydrogen peroxide, reacted with phosphorus oxychloride under the catalysis of triethylamine, and chlorinated to synthesize 2-chloronicotinic acid (US4144238); the yield of this method is 80%, and the obtained The product has high purity, but there is a large amount of waste acid, which seriously pollutes the environment
[0005] (2) Use 3-cyanopyridine as raw material, carry out N-oxidation through hydrogen peroxide, react with phosphorus oxychloride under the catalysis of triethylamine, and chlorinate to obtain 2-chloro-3-cyanopyridine, and the product is catalyzed by alkali Hydrolysis, synthesis of 2-chloronicotinic acid (JP169672), the yield of this method is low, generally 50-60%, and the catalyst is expensive, and a large amount of acidic wastewater will be generated during production, causing environmental pollution, which is not suitable for large-scale industrialization Production
The process route is simple and the reaction conditions are mild, but the price of the oxidant is high, the consumption is large, the cost is high, and a large amount of waste water is produced, so it is not suitable for large-scale industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 250mL four-neck flask equipped with a mechanical stirrer and a thermometer, add 25.5g (0.2mol) of 2-chloro-3-picoline, 100mL of glacial acetic acid and 2.5g (0.01mol) of manganese acetate. Stir at room temperature, and feed 5.4L (0.24mol) of ozone produced by an ozone generator. After 5 hours, a large amount of white solids are produced in the reaction solution. TLC monitors the reaction process. After 1 / 3 of the mixture was filtered and dried to obtain 23.5 g of white solid product, the yield was 98%, and the melting point was 176-178°C.

Embodiment 2

[0024] In a 250 mL four-necked flask equipped with a mechanical stirrer and a thermometer, 25.5 g (0.2 mol) of 2-chloro-3-picoline, 100 mL of tetrahydrofuran and 5 g (0.02 mol) of manganese acetate were added. Stir at 50°C, feed 8.96L (0.4mol) of ozone generated by an ozone generator, and monitor the reaction process by TLC. After the reaction, filter THF under reduced pressure to obtain a crude product, recrystallize from ethyl acetate, and dry to obtain a white solid product 23.2g, 97% yield, melting point 175-178°C.

Embodiment 3

[0026] In a 250 mL four-neck flask equipped with a mechanical stirrer and a thermometer, 25.5 g (0.2 mol) of 2-chloro-3-picoline, 100 mL of toluene and 1.83 g (0.01 mol) of zinc acetate were added. Stir at 100°C, feed 13.44 L (0.6 mol) of ozone generated by an ozone generator, and monitor the reaction progress by TLC. After the reaction is completed, toluene is filtered under reduced pressure to obtain a crude product, which is recrystallized from ethyl acetate and dried to obtain a white solid. The product is 21.5g, the yield is 90%, and the melting point is 175-177°C.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a method for synthesizing a 2-chloronicotinic acid by one-step oxidation, and belongs to the field of chemical synthesis. By adopting the method, 2-chloro-3-alkyl pyridine or 2-chloro-3-olefin pyridine is adopted as an initial material, acetate is taken as a catalyst, ozone is generated by an ozone generator is led, and the product 2-chloronicotinic acid is obtained under the condition of which the reaction temperature is 20-100 DEG C. The 2-chloronicotinic acid is simple and available in used raw material, low in cost, simple in process, and less in pollution, and accords with the development requirements of green chemistry.

Description

technical field [0001] The invention belongs to the fields of chemical industry and pesticides, in particular to a method for synthesizing 2-chloronicotinic acid through one-step oxidation. Background technique [0002] 2-Chloronicotinic acid is an important intermediate of medicine and pesticide. It can be used in pesticides to synthesize fungicides, insecticides and herbicides, such as nicosulfuron, diflufenican, etc.; used in medicine to synthesize many medical antibiotics and drugs for treating cardiovascular diseases. Because of its wide range of biochemical effects, the research on its synthesis process has aroused people's widespread interest. [0003] There are many preparation routes for 2-chloronicotinic acid, and the most studied synthetic routes mainly include the following: [0004] (1) Niacin is used as the starting material for N-oxidation with hydrogen peroxide, reacted with phosphorus oxychloride under the catalysis of triethylamine, and chlorinated to syn...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/807C07D213/80
CPCC07D213/80C07D213/807
Inventor 杨寿海丁永山罗中华薛谊何小强龚东平岳洪亮
Owner NANJING REDSUN BIOCHEM CO LTD
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com