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Synthesis method of 4-picolyl chloride hydrochloride

A technology of chloromethylpyridine hydrochloride and synthesis method, which is applied in the field of synthesis of 4-chloromethylpyridine hydrochloride, can solve the problems of high reagent toxicity and high cost, and achieve few reaction steps, low cost and high yield high effect

Inactive Publication Date: 2019-05-17
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 invention is to overcome the high cost and high toxicity of reagents in the prior art, and provide a synthetic method of 4-chloromethylpyridine hydrochloride with low cost, high yield and mild reaction conditions

Method used

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  • Synthesis method of 4-picolyl chloride hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1) Add 4-picoline (18.6g, 0.2mol), 150ml of water to a 250ml flask, heat to 80℃, add potassium permanganate (66.36g, 0.42mol) in batches, and maintain the temperature at 75- Heat and stir at 80°C for 35 minutes, followed by thin-layer chromatography. After the reaction is complete, adjust the pH value of the reaction solution to 3 with 2mol / l hydrochloric acid, and cool the temperature of the reaction solution to 25°C to obtain 4-picolinic acid by suction filtration.

[0021] (2) 4-picolinic acid and methanol (12g, 0.26mol) under the action of concentrated sulfuric acid produce methyl 4-picolinate.

[0022] (3) Methyl 4-picolinate was dissolved in a solvent mixed with 75ml THF and 75ml toluene, sodium borohydride (30.24g, 0.8mol) and aluminum trichloride were added in batches at 0-5°C, and the reaction was continued after the addition 3 -4h, TLC tracking analysis until the reaction is complete to obtain 4-pyridine methanol.

[0023] (4) After 4-pyridine methanol is reacted w...

Embodiment 2

[0025] (1) Add 4-picoline (18.6g, 0.2mol), 150ml of water into a 250ml flask, heat to 80℃, add potassium permanganate (69.5g, 0.44mol) in batches, and maintain the temperature at 75- Heat and stir at 80°C for 35 minutes, followed by thin-layer chromatography. After the reaction is complete, adjust the pH value of the reaction solution to 4 with 2mol / l hydrochloric acid, and cool the temperature of the reaction solution to 25°C to obtain 4-picolinic acid by suction filtration.

[0026] (2) 4-picolinic acid and methanol (12g, 0.26mol) under the action of concentrated sulfuric acid produce methyl 4-picolinate.

[0027] (3) Methyl 4-picolinate was dissolved in a solvent mixed with 75ml THF and 75ml toluene, sodium borohydride (34g, 0.9mol) and aluminum trichloride were added in batches at 0-5°C, and the reaction was continued after the addition 3- 4h, TLC traced analysis until the reaction was completed to obtain 4-pyridine methanol.

[0028] (4) After 4-pyridine methanol is reacted wit...

Embodiment 3

[0030] (1) Add 4-methylpyridine (18.6g, 0.2mol), 150ml of water to a 250ml flask, heat to 80℃, add potassium permanganate (72.7g, 0.46mol) in batches, and maintain the temperature at 75- Heat and stir at 80°C for 35 minutes, followed by thin-layer chromatography. After the reaction is complete, adjust the pH value of the reaction solution to 4 with 2mol / l hydrochloric acid, and cool the temperature of the reaction solution to 25°C to obtain 4-picolinic acid by suction filtration.

[0031] (2) 4-picolinic acid and methanol (12g, 0.26mol) under the action of concentrated sulfuric acid produce methyl 4-picolinate.

[0032] (3) Methyl 4-picolinate was dissolved in a solvent mixed with 75ml THF and 75ml toluene, sodium borohydride (37.8g, 1.0mol) and aluminum trichloride were added in batches at 0-5°C, and the reaction was continued after the addition 3 -4h, TLC tracking analysis until the reaction is complete to obtain 4-pyridine methanol.

[0033] (4) After 4-pyridine methanol is react...

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of 4-picolyl chloride hydrochloride. The method comprises following steps: (1), 4-methylpyridineis taken as a raw material, water is taken as a solvent, 4-methylpyridine is oxidized into 4-picolinic acid by potassium permanganate, wherein a mole ratio of 4-methylpyridine to potassium permanganate is 1:(2.1-2.3), the oxidization temperature is 75-80 DEG C, heating is performed for 35 min, a reaction solution is regulated to be acidic after complete reaction and then is cooled and filtered, and 4-picolinic acid is obtained; (2), methyl pyridine-4-carboxylate is produced from 4-picolinic acid and methanol under the acidic condition, and a mole ratio of 4-picolinic acid to methanol is 1:1.3; (3), methyl pyridine-4-carboxylate is reduced into 4-pyridinemethanol; (4), 4-pyridinemethanol and thionyl chloride are subjected to a reaction, a target product 4-picolyl chloride hydrochloride isobtained, and a mole ratio of 4-pyridinemethanol to thionyl chloride is 1: (1.1-1.3).

Description

Technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a method for synthesizing 4-chloromethylpyridine hydrochloride. Background technique [0002] Chloromethylpyridine hydrochloride is an important chemical raw material for various pesticides, pharmaceutical intermediates, pesticides, herbicides, and fungicides. The current production method uses pyridine to directly methylate, uses methyl lithium and other precious metal chemical raw materials, and then ventilates chlorine to carry out the chlorination reaction. After pyridine chloromethylation, it is easier to connect other groups to synthesize high value-added chemical raw material intermediates and APIs. However, the use of methyl lithium and other materials as raw materials brings great cost and price pressure, and it is more troublesome to recover precious metals. Using dimethyl sulfate is more toxic and dangerous for operators. Summary of the invention [0003] The pu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/26
Inventor 魏倩
Owner 丹阳市中润检测技术有限公司