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A kind of preparation method of flometoquin

A technology of ethyl and dimethyl, applied in the field of preparation of flometoquin, can solve the problems of complicated post-processing and large amount of solvent recovery, and achieve the effects of simplifying post-processing operations, improving yield and purity, and improving environmental protection benefits.

Active Publication Date: 2021-12-14
湖南速博生物技术有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The main purpose of the present invention is to provide the preparation of 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)-1,4-dihydroquinolin-4-yl The improved method of methyl carbonate overcomes the problems of using a large amount of toxic, harmful and expensive raw materials in the prior art, complex post-treatment, large amount of solvent recovery, and generation of a large amount of waste water, and provides a product with simple process, no need for recrystallization, low production cost, and Preparation method of flometoquin with high purity and yield

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  • A kind of preparation method of flometoquin

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Embodiment 1

[0021] 30.0 g of 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)-1,4-dihydroquinolin-4-ol (0.079 mol), Add 60.0 g of dimethyl carbonate and 1.2 g of sodium tert-butoxide into a 250 mL three-necked flask, connect the flask to the inlet of a type A molecular sieve pervaporation inorganic membrane device, stir and heat to reflux, and keep it warm for 4.0 h. During the reaction, the organic vapor in the The mixture of methanol and water passes through the A-type molecular sieve to infiltrate and vaporize the inorganic membrane tube to separate the system, and the solvent is condensed and refluxed back to the kettle for reaction. At the end of the reaction, a total of 2.6 g of methanol and water were collected. The reaction solution was lowered to room temperature, washed once with water, and the organic phase was concentrated and dried to obtain 33.1 g of white solid with a content of 98.9% (external standard of liquid chromatography) and a yield of 95.4% (using 2-ethyl-3,7-d...

Embodiment 2

[0023] 30.0 g of 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)-1,4-dihydroquinolin-4-ol (0.079 mol), Add 150.0 g of dimethyl carbonate and 1.8 g of sodium tert-butoxide into a 250 mL three-neck flask, connect the flask to the inlet of a type A molecular sieve pervaporation inorganic membrane device, stir and heat to reflux, and keep the reaction for 4.0 h. During the reaction, the organic vapor in the The mixture of methanol and water passes through the A-type molecular sieve to infiltrate and vaporize the inorganic membrane tube to separate the system, and the solvent is condensed and refluxed back to the kettle for reaction. At the end of the reaction, a total of 3.8 g of methanol and water were collected. The reaction solution was lowered to room temperature, washed once with water, and the organic phase was concentrated and dried to obtain 33.4 g of white solid with a content of 99.2% (external standard of liquid chromatography) and a yield of 96.7% (based on 2-ethy...

Embodiment 3

[0025] 30.0 g of 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)-1,4-dihydroquinolin-4-ol (0.079 mol), Add 90.0 g of dimethyl carbonate and 1.8 g of sodium tert-butoxide into a 250 mL three-necked flask, connect the flask to the inlet of a type A molecular sieve pervaporation inorganic membrane device, stir and heat to reflux, and keep the temperature for 4.0 h. During the reaction, the organic vapor in the The mixture of methanol and water passes through the A-type molecular sieve to infiltrate and vaporize the inorganic membrane tube to separate the system, and the solvent is condensed and refluxed back to the kettle for reaction. At the end of the reaction, a total of 2.7 g of methanol and water were collected. The reaction solution was lowered to room temperature, washed once with water, and the organic phase was concentrated and dried to obtain 33.5g of white solid with a content of 98.8% (external standard of liquid chromatography) and a yield of 96.5% (using 2-ethy...

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Abstract

A preparation method for flometoquin, under the action of catalyst, raw material 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)-1,4-dihydro Quinoline-4-alcohol is refluxed in dimethyl carbonate, and the methanol produced by the reaction is removed by a gas permeable membrane. After the reaction is completed, it is cooled to room temperature, washed with water, and the organic phase is concentrated and dried to obtain 2-ethyl-3,7-di Methyl-6-(4-(trifluoromethoxy)phenoxy)-1,4-dihydroquinolin-4-yl methyl carbonate, the yield reached 96.7%, and the product content reached 99.2% (LC external standard). The preparation method has the advantages of simple process, no need of distillation, high product purity and yield.

Description

technical field [0001] The invention relates to a preparation method of flometoquin. More specifically, the present invention relates to an improved and simplified process for the preparation of flometoquin. Background technique [0002] Flometoquin is a novel quinoline insecticide jointly developed by Meiji Pharmaceutical Co., Ltd. and Nippon Kayaku Co., Ltd. It has a novel mechanism of action and can be used to control pests that are resistant to existing insecticides. The agent mainly has an excellent control effect on Thysanoptera pests (thrips), whiteflies, gall moths and small Lepidoptera pests, and has a fast killing speed and a long-lasting effect. [0003] "Synthesis of the Novel Quinoline Insecticide Flometoquin", Liu Anchang, Bao Yang, Huang Shixiang, Li Qi, Deng San, Journal of Wuhan Engineering University, Vol. 3, Vol. 41, Page 238-241, June 2019, in ter Under the action of potassium butoxide, 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4-ol a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/22
CPCC07D215/22
Inventor 杨紫冬谭悦田轮陈三龙刘林波
Owner 湖南速博生物技术有限公司