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5-chloro-2,3-dihydro-1-indanone preparation method

A dihydro, indanone technology, applied in the field of medicine and chemical industry, can solve the problems of difficult post-processing, inconvenient operation, high energy consumption, and achieve the effects of reducing the generation of high-temperature polymers, increasing the yield, and reducing the reaction temperature

Active Publication Date: 2019-02-01
四平市精细化学品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the disadvantages of high energy consumption, large pollution, inconvenient operation, and difficult post-processing.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Throw 225g (2.0mol) of chlorobenzene into a 1000mL four-necked bottle, throw 332g (2.5mol) of aluminum trichloride under stirring, add 254g of 3-chloropropionyl chloride dropwise at 30°C, react for 3 hours, and then add it to the molten The mass ratio is 6:3.5:0.5 in aluminum trichloride, sodium chloride, potassium chloride mixture 332g. The temperature was raised to 110° C. for 3 hours, the conversion rate was 97%, and the reaction was completed. The reaction feed solution was added to ice water for hydrolysis, filtered, and dried to obtain 330.2 g of a brown solid, which was refined to obtain 249.3 g of light yellow powder 5-chloro-2,3-dihydro-1-indanone, and the content was detected by high pressure liquid chromatography It is 99.2%, and the yield is 74.8%.

Embodiment 2

[0050]Throw 225g (2.0mol) of chlorobenzene into a 1000mL four-necked bottle, throw 332g (2.5mol) of aluminum trichloride under stirring, add 254g of 3-chloropropionyl chloride dropwise at 30°C, react for 3 hours, and then add it to the molten The mass ratio is 6.5:3:0.5 in aluminum trichloride, sodium chloride, potassium chloride mixture 332g. The temperature was raised to 130° C. for 3 hours, the conversion rate was 98%, and the reaction was completed. The reaction feed solution was added to ice water for hydrolysis, filtered, and dried to obtain 335 g of a brown solid, which was refined to obtain 250.1 g of light yellow powder 5-chloro-2,3-dihydro-1-indanone, and the content detected by high pressure liquid chromatography was 99.5%, yield 75%.

Embodiment 3

[0052] Throw 225g (2.0mol) of chlorobenzene into a 1000mL four-necked bottle, throw 332g (2.5mol) of aluminum trichloride under stirring, add 254g of 3-chloropropionyl chloride dropwise at 30°C, react for 3 hours, and then add it to the molten Remove in 332g of aluminum trichloride and sodium chloride mixture with a mass ratio of 7:3. The temperature was raised to 150° C. for 3 hours, the conversion rate was 95%, and the reaction was completed. The reaction feed solution was added to ice water for hydrolysis, filtered, and dried to obtain 335 g of a brown solid, which was refined to obtain 217.4 g of light yellow powder 5-chloro-2,3-dihydro-1-indanone, and the content detected by high pressure liquid chromatography was 99.3%, yield 65.2%. see figure 1 and figure 2 , figure 1 It is the HPLC of 5-chloro-2,3-dihydro-1-indanone standard substance, figure 2 High performance liquid chromatogram of 5-chloro-2,3-dihydro-1-indanone prepared for Example 3.

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Abstract

The invention provides a 5-chloro-2,3-dihydro-1-indanone preparation method, which comprises: carrying out a reaction by using chlorobenzene and 3-chloro-propionyl chloride as raw materials and usinga mixed molten salt as catalyst and a solvent to obtain 5-chloro-2,3-dihydro-1-indanone, wherein the mixed molten salt is a mixture comprising any two or three materials selected from potassium chloride, sodium chloride and aluminum chloride. According to the present invention, the mixed molten salt potassium chloride-sodium chloride-aluminum chloride is used as the catalyst, and becomes liquid ata temperature of about 100 DEG C, such that the problem that aluminum chloride is sublimated before melting is solved; and the mixed molten salt potassium chloride-sodium chloride-aluminum chloride is simultaneously used as the catalyst and the solvent in the reaction of chlorobenzene and 3-chloro-propionyl chloride, such that the conversion rate of the reaction can achieve 98% at the temperatureof 120-130 DEG C, and the yield of 5-chloro indanone can achieve 75%.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a preparation method of 5-chloro-2,3-dihydro-1-indanone. Background technique [0002] 5-Chloro-2,3-dihydro-1-indanone, referred to as 5-chloroindanone, is an important intermediate of indoxacarb, a new pesticide variety of DuPont Company in the United States. It is also a benzoyl indole anti-inflammatory drug and amino Important pharmaceutical intermediates of acetyl anticoagulants and other drugs. The synthetic route of the currently disclosed 5-chloroindanone has the following types: [0003] The first synthetic route (using m-chlorocinnamic acid as the synthetic method of raw material): [0004] The route uses m-chlorocinnamic acid as a raw material, which is hydrogenated to obtain m-chlorophenylpropionic acid, chlorinated to obtain m-chlorophenylpropionyl chloride, and finally cyclized to obtain 5-chloroindanone. The disadvantage of this...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/697C07C49/80C07C45/46
CPCC07C45/46C07C2602/08C07C49/80C07C49/697
Inventor 薛李冰刘长宝刘丽娟石臣志纪红岩王春艳李永生李亚杰郑伟东
Owner 四平市精细化学品有限公司
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