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Synthesis method of flometoquin intermediate

A synthesis method and intermediate technology, applied in the field of organic synthesis, can solve problems such as intractable solid waste, and achieve the effects of good environmental protection benefit, low production cost and simple operation.

Active Publication Date: 2020-10-23
湖北中迅长青科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention is mainly for overcoming the traditional two-step synthesis process of flometoquin intermediate 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4-alcohol Using a large amount of metals or polymetallic salts as reducing agents will generate a large amount of difficult-to-handle solid waste. A one-pot synthesis method is provided. The method is simple to operate, low in production cost, less in solid waste, easy to handle, and less polluting to the environment.

Method used

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  • Synthesis method of flometoquin intermediate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add solvent 156.00 g toluene, 3.90 g catalyst Pt / C (3%, humidity 60%), 0.16 g catalyst methanesulfonic acid, 15.60 g (49.80 mmol) 2-methyl-4 -Nitro-1-(4-(trifluoromethoxy)phenoxy)benzene and 8.70 g (54.99 mmol) ethyl 2-methyl-3-oxopentanoate, pressurized to 0.05 MPa with hydrogen, And reflux water separation reaction under this pressure, high performance liquid chromatography monitors the reaction end point, the reaction temperature is finally 123 ℃, after the reaction is completed, the reaction solution is cooled to room temperature, the catalyst Pt / C is recovered by filtration, the filtrate is poured into water, adjusted with hydrochloric acid pH to 5, precipitated white solid, filtered, dried to obtain 16.96 g of product, content 95.5%, yield ≥ 86.2% (with 2-methyl-4-nitro-1-(4-(trifluoromethoxy) phenoxy) benzene).

Embodiment 2

[0019] Add solvent 46.80 g toluene, 0.39 g catalyst Pt / C (3%, humidity 60%), 0.03 g catalyst methanesulfonic acid, 15.60 g (49.80 mmol) 2-methyl-4 -Nitro-1-(4-(trifluoromethoxy)phenoxy)benzene and 8.15 g (51.52 mmol) ethyl 2-methyl-3-oxopentanoate, pressurized to 0.10 MPa with hydrogen, And reflux water separation reaction under this pressure, high performance liquid chromatography monitors the reaction end point, the reaction temperature is finally 135 ℃, after the reaction is completed, the reaction solution is cooled to room temperature, the catalyst Pt / C is recovered by filtration, the filtrate is poured into water, adjusted with hydrochloric acid When the pH reached 5, a white solid was precipitated, filtered, and dried to obtain 17.01 g of the product, with a content of 95.0%, and a yield of ≥ 86.0% (with 2-methyl-4-nitro-1-(4-(trifluoromethoxy) phenoxy) benzene).

Embodiment 3

[0021] Add solvent 78.00 g toluene, 3.90 g catalyst Pt / C (3%, humidity 60%), 0.06 g catalyst methanesulfonic acid, 15.60 g (49.80 mmol) 2-methyl-4 -Nitro-1-(4-(trifluoromethoxy)phenoxy)benzene and 8.38 g (52.97 mmol) ethyl 2-methyl-3-oxopentanoate, pressurized to 0.01 MPa with hydrogen, And reflux water separation reaction under this pressure, the end point of the reaction is monitored by high performance liquid chromatography, the reaction temperature is finally 114 ° C, after the reaction is completed, the reaction solution is cooled to room temperature, the catalyst Pt / C is recovered by filtration, the filtrate is poured into water, adjusted with hydrochloric acid pH to 5, a white solid was precipitated, filtered, and dried to obtain 16.99 g of product, content 95.9%, yield ≥ 86.7% (with 2-methyl-4-nitro-1-(4-(trifluoromethoxy) phenoxy) benzene).

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Abstract

The invention relates to a synthesis method of a flometoquin intermediate 2-ethyl-3, 7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinoline-4-ol. According to the invention, toluene is used as a solvent,Pt / C and methanesulfonic acid are used as catalysts, 2-methyl-4-nitro-1-(4-(trifluoromethoxy)phenoxy)benzene and 2-methyl-3-oxoethyl valerate are adopted as the raw materials, hydrogen is introducedinto a pressure kettle with backflow water diversion function for pressurization reaction, traditional two operation units of reduction and ring closing are changed into a one-pot method, operation iseasy, the production cost is low, the solid waste amount is small, treatment is easy, environmental pollution is small, and the method has important significance in industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a one-pot synthesis of flometoquin intermediate 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinoline -4-ol method. Background technique [0002] 2-Ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4-ol is a white solid and is an important intermediate in the synthesis of flometoquin. [0003] Flometoquin is a new type of quinoline insecticide and acaricide jointly developed by Japan Meiji Seika Kaisha Company (now Meiji Seika Pharma Company) and Nippon Kayaku Company and reported in 2004. In June 2011, the English common name was approved by ISO, and it was listed in Japan after registration in 2018. Its chemical structure is novel, and its mechanism of action and site are unique. It is mainly used to control small piercing-sucking pests. It is effective against Thysanoptera, Hemiptera, Coleoptera, Acari, Lepidoptera, Hymenoptera, Orthoptera, Dipter...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/22
CPCC07D215/22
Inventor 胡志彬杨紫冬田轮龚小丽
Owner 湖北中迅长青科技有限公司
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