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Synthesis method of cloquintocet-mexyl

A synthesis method and the technology of quintoquin, which are applied in the synthesis of herbicide safeners and the synthesis of quinquinol, can solve the problems of low reaction yield and influence on product yield, and achieve simple operation, easy industrial production, and mild reaction Effect

Pending Publication Date: 2021-07-20
甘肃联凯生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the above-mentioned route, the transesterification reaction of 5-chloro-8-quinolineoxyacetic acid methyl ester and 2-heptanol is an equilibrium reaction, so this step reaction yield is lower, and in the process of transesterification, when temperature When the temperature is higher than 60°C, 5-chloro-8-oxoquinoline acetic acid methyl ester is easy to decompose to generate 5-chloro-8-oxoquinoline acetic acid, which greatly affects the yield of the product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Throw 35.8g of 5-chloro-8-hydroxyquinoline, 75g of DMF, and 24g of methyl chloroacetate into a 500ml four-necked bottle, start stirring, raise the temperature to 60°C, add 35.8g of potassium carbonate in batches, raise the temperature to 75°C, and keep warm for half an hour before raising the temperature Incubate at 80-82°C for 2 hours, sample HPLC to detect that the quinoline content is less than 0.5%, and the reaction is complete. Add 1000ml of water into a 2000ml beaker, start stirring, pour the reaction solution while hot, stir for half an hour, and filter with suction. The filter cake was put into a 500ml single-necked round-bottomed flask, and was rotary evaporated until no water flowed out, weighing 42.6g, and the yield was 85%.

[0025] Put 12g caustic soda into a 500ml four-necked bottle, start stirring with 240g water, after the caustic soda dissolves, add 50g methyl 5-chloro-8-oxyquinoline acetate (dried), heat up and control the temperature at 60-65°C for on...

Embodiment 2

[0028] Put 35.8g of 5-chloro-8-hydroxyquinoline (1eq), 64gDMF, 21.6g of methyl chloroacetate (1eq) into a 500ml four-necked bottle, start stirring, raise the temperature to 60°C, add 35.8g of potassium carbonate in batches, and raise the temperature to 75 ℃, keep warm for half an hour, then raise the temperature to 80-82 ℃ and keep warm for 1 hour, sample HPLC to detect that the quinoline content is less than 0.5%, and the reaction is over. Add 1000ml of water into a 2000ml beaker, start stirring, pour the reaction solution while hot, stir for half an hour, and filter with suction. The filter cake was put into a 500ml single-necked round-bottomed flask, and rotary steamed until no water flowed out, weighing 39.6g, and the yield was 79%.

[0029] Throw 10.3g caustic soda (1.3eq) into a 500ml four-necked bottle, start stirring with 240g water, after the caustic soda is dissolved, add 50g methyl 5-chloro-8-oxyquinoline acetate (1eq, dry), raise the temperature to control the temp...

Embodiment 3

[0032] Put 35.8g of 5-chloro-8-hydroxyquinoline (1eq), 79g of DMF, 26g of methyl chloroacetate (1.2eq) into a 500ml four-necked bottle, start stirring, raise the temperature to 60°C, add 35.8g of potassium carbonate in batches, and raise the temperature to 75 ℃, keep warm for half an hour, then raise the temperature to 80-82 ℃ and keep warm for 1 hour, sample HPLC to detect that the quinoline content is less than 0.5%, and the reaction is over. Add 1000ml of water into a 2000ml beaker, start stirring, pour the reaction solution while hot, stir for half an hour, and filter with suction. The filter cake was put into a 500ml single-necked round-bottomed flask, and rotary steamed until no water flowed out, weighing 45.1g, and the yield was 90%.

[0033] Throw 14.3g caustic soda (1.8eq) into a 500ml four-necked bottle, start stirring with 240g water, after the caustic soda is dissolved, add 50g methyl 5-chloro-8-oxyquinoline acetate (1eq, dry), and control the temperature by raisin...

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Abstract

The invention discloses a cloquintocet-mexyl synthesis method which comprises the following steps: (1) preparing methyl 5-chloro-8-quinolinoxyacetate by taking 5-chloro-8-hydroxyquinoline and methyl chloroacetate as raw materials, DMF (Dimethyl Formamide) as a solvent and potassium carbonate as an acid-binding agent; (2) carrying out alkaline hydrolysis on the methyl 5-chloro-8-quinolinoxyacetate prepared in the step (1), and then carrying out acid precipitation to prepare 5-chloro-8-quinolinoxyacetic acid; and (3) carrying out esterification reaction on the 5-chloro-8-quinolinoxyacetic acid prepared in the step (2) and 2-heptanol to prepare cloquintocet-mexyl. On the basis of an existing common industrial process, the prepared methyl 5-chloro-8-quinolinoxyacetate is hydrolyzed into 5-chloro-8-quinolinoxyacetic acid and then esterification reaction is conducted on the 5-chloro-8-quinolinoxyacetic acid and 2-heptanol to prepare cloquintocet-mexyl. The product yield is improved, the process is simple, and industrial production is easy.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to the synthesis of a herbicide safener, in particular to a method for synthesizing acetoquine. Background technique [0002] Jieduquine, also known as clofenacyl, has a chemical name of 1-methylhexyl (5-chloro-8-quinolineoxy) acetate. Jieduquine can be used as an intermediate in medicine and organic synthesis in industry. As a heterocyclic herbicide safener, it is the antidote corresponding to the herbicide clodinafop-propargyl, preventing the damage of clodinafop-propargyl to small-grained grains and expanding the application range of clodinafop-propargyl. Currently, clodinafop-propargyl has been commercialized and widely used use. [0003] Now the industry mainly uses 5-chloro-8-hydroxyquinoline as raw material to prepare quinolin, and the common process is as follows: 5-chloro-8-hydroxyquinoline reacts with methyl chloroacetate to generate 5-chloro-8-quinoline Methyl a...

Claims

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Application Information

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IPC IPC(8): C07D215/28
CPCC07D215/28
Inventor 赵飞四任永辉覃能东蒋云翔
Owner 甘肃联凯生物科技有限公司
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