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Synthesis method of 3-chloromethylpyridine hydrochloride

The technology of a chloromethylpyridine hydrochloride and a synthesis method is applied in the field of synthesis of 3-chloromethylpyridine hydrochloride, can solve the problems of expensive reagents, high reagent toxicity, etc., and achieves low cost and few reaction steps. , the effect of high yield

Inactive Publication Date: 2019-05-14
丹阳市中润检测技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to overcome the disadvantages of high cost and high toxicity of reaction reagents in the prior art, and provide a synthetic method of 3-chloromethylpyridine hydrochloride with low cost, high yield and mild reaction conditions

Method used

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  • Synthesis method of 3-chloromethylpyridine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (1) Add 3-picoline (18.6g, 0.2mol) and 150ml of water into a 250ml flask, heat to 80°C, add potassium permanganate (66.36g, 0.42mol) in batches, and maintain the temperature at 85- Heat and stir at 90°C for 30min, track and analyze by thin layer chromatography, adjust the pH value of the reaction solution to 3 with 2mol / l hydrochloric acid after the reaction is complete, cool the temperature of the reaction solution to 25°C and suction filter to obtain 3-pyridinecarboxylic acid.

[0022] (2) 3-pyridinecarboxylic acid and methanol (12g, 0.26mol) were reacted with concentrated sulfuric acid to generate 3-picolinic acid methyl ester.

[0023] (3) Methyl 3-pyridinecarboxylate was dissolved in a solvent mixed with 75ml THF and 75ml toluene, and sodium borohydride (30.24g, 0.8mol) and aluminum trichloride were added in batches at 0-5°C, and the reaction continued for 3 -4h, TLC tracking analysis until the reaction is complete to get 3-pyridinemethanol.

[0024] (4) 2-pyridin...

Embodiment 2

[0026] (1) Add 3-picoline (18.6g, 0.2mol) and 150ml of water into a 250ml flask, heat to 80°C, add potassium permanganate (69.5g, 0.44mol) in batches, and maintain the temperature at 85- Heat and stir at 90°C for 30 minutes, follow-up analysis by thin-layer chromatography, adjust the pH value of the reaction solution to 4 with 2mol / l hydrochloric acid after the reaction is complete, cool the temperature of the reaction solution to 25°C and suction filter to obtain 3-pyridinecarboxylic acid.

[0027] (2) 3-pyridinecarboxylic acid and methanol (12g, 0.26mol) were reacted with concentrated sulfuric acid to generate 3-picolinic acid methyl ester.

[0028] (3) Methyl 3-pyridinecarboxylate was dissolved in a solvent mixed with 75ml THF and 75ml toluene, and sodium borohydride (34g, 0.9mol) and aluminum trichloride were added in batches at 0-5°C, and the reaction was continued after adding 3- 4h, TLC follow-up analysis until the reaction is complete to get 3-pyridinemethanol.

[002...

Embodiment 3

[0031] (1) Add 3-picoline (18.6g, 0.2mol) and 150ml of water into a 250ml flask, heat to 80°C, add potassium permanganate (72.7g, 0.46mol) in batches, and maintain the temperature at 85- Heating and stirring at 90°C for 30 minutes, followed by thin-layer chromatography analysis, after the reaction is complete, use 2mol / l hydrochloric acid to adjust the pH value of the reaction solution to 4, and cool the temperature of the reaction solution to 25°C to obtain 3-pyridinecarboxylic acid by suction filtration.

[0032] (2) 3-pyridinecarboxylic acid and methanol (12g, 0.26mol) were reacted with concentrated sulfuric acid to generate 3-picolinic acid methyl ester.

[0033] (3) Methyl 3-pyridinecarboxylate was dissolved in a solvent mixed with 75ml THF and 75ml toluene, and sodium borohydride (37.8g, 1.0mol) and aluminum trichloride were added in batches at 0-5°C, and the reaction continued for 3 -4h, TLC tracking analysis until the reaction is complete to get 3-pyridinemethanol.

...

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Abstract

The invention belongs to the field of organic chemistry, and particularly relates to a synthesis method of 3-chloromethylpyridine hydrochloride. The synthesis method includes following steps: (1), taking 3-methylpyridine as a raw material and water as a solvent, and using potassium permanganate to oxidize the raw material to be 3-pyridine carboxylic acid: maintaining oxidizing temperature at 85-90DEG C, heating for 30min, adjusting reaction liquid to be acidic after reaction is finished, cooling, and filtering to obtain 3-pyridine carboxylic acid, wherein a molar ratio of 3-methylpyridine topotassium permanganate is 1:2.1-2.3; (2), allowing 3-pyridine carboxylic acid and methanol in an acidic condition to generate 3-methyl pyridine carboxylate, wherein a molar ratio of 3-pyridine carboxylic acid to methanol is 1:1.3; (3), reducing 3-methyl pyridine carboxylate to be 3-pyridinemethanol; (4), allowing 3-pyridinemethanol and thionyl chloride to react to obtain a target product-3-chloromethylpyridine hydrochloride, wherein a molar ratio of 3-pyridinemethanol to thionyl chloride is 1:1.1-1.3.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a method for synthesizing 3-chloromethylpyridine hydrochloride. Background technique [0002] Chloromethylpyridine hydrochloride is an important chemical raw material for various pesticides, pharmaceutical intermediates, insecticides, herbicides, and fungicides. The current production method adopts pyridine to directly add methyl groups, uses precious metal chemical raw materials such as methyl lithium, and then passes chlorine gas to carry out chlorination reaction. After pyridine chloromethylation, it is easier to connect other groups to synthesize chemical raw material intermediates and raw materials with high added value. However, the use of methyllithium as a raw material has high cost and price pressures, and it is troublesome to recover precious metals. Dimethyl sulfate is highly toxic and dangerous to operators. Contents of the invention [0003] The purpose of the pr...

Claims

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Application Information

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IPC IPC(8): C07D213/26
Inventor 魏倩
Owner 丹阳市中润检测技术有限公司
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