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Preparation method of 2-methyl-6-chloromethylpyridinehydrochloride

A technology of chloromethylpyridine hydrochloride and methyl, which is applied in the field of preparation of 2-methyl-6-chloromethylpyridine hydrochloride, can solve the problems of long route and high cost of raw materials, achieves high yield, The effect of low cost and few steps

Inactive Publication Date: 2015-10-14
黄荣辉
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the invention is to overcome the technical deficiencies of high raw material cost and long route in the prior art, and provide a kind of preparation method of 2-methyl-6-chloromethylpyridine hydrochloride

Method used

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  • Preparation method of 2-methyl-6-chloromethylpyridinehydrochloride

Examples

Experimental program
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Embodiment 1

[0020] Add 9.3g of 2-picoline and 60ml of methanol into a 500ml three-necked flask, add 1.3g of aluminum trichloride, cool to below 0°C and dropwise add 7.8g of acetyl chloride, after the dropwise addition, heat up to a reaction temperature of 50-100°C , reflux reaction for 6 hours, sampling analysis, until the raw material 2-picoline reacted completely; add 1.9g of sodium borohydride to the system, the reaction temperature is 60 ℃, carry out reduction reaction, react for 6 hours, filter, remove inorganic salts, filtrate Distill off methanol, extract 2-methyl-6-hydroxymethylpyridine with dichloromethane, dry with anhydrous sodium sulfate, cool to -10°C and start adding 6g of thionyl chloride dropwise, then naturally warm to room temperature for reaction 2 -3 hours, 2-methyl-6-chloromethylpyridine hydrochloride was obtained, and the total yield was 82%.

Embodiment 2

[0022] Add 9.3g of 2-picoline and 60ml of methanol into a 500ml three-necked flask, add 1.3g of aluminum trichloride, cool to below 0°C and dropwise add 7.8g of acetyl chloride, after the dropwise addition, heat up to a reaction temperature of 50-100°C , reflux reaction for 5 hours, sampling analysis, until the raw material 2-picoline reacted completely; add 1.9g of sodium borohydride to the system, the reaction temperature is 50 ℃, carry out the reduction reaction, react for 5 hours, filter, remove inorganic salts, filtrate Distill methanol off, extract 2-methyl-6-hydroxymethylpyridine with dichloromethane, dry with anhydrous sodium sulfate, cool to -20°C and start adding 6g of thionyl chloride dropwise, then naturally warm to room temperature for reaction 2 -3 hours, 2-methyl-6-chloromethylpyridine hydrochloride was obtained, and the total yield was 78%.

Embodiment 3

[0024] Add 9.3g of 2-picoline and 60ml of methanol into a 500ml three-necked flask, add 1.3g of aluminum trichloride, cool to below 0°C and dropwise add 7.8g of acetyl chloride, after the dropwise addition, heat up to a reaction temperature of 50-100°C , reflux reaction for 10 hours, sampling analysis, until the raw material 2-picoline reacted completely; add 1.9g of sodium borohydride to the system, the reaction temperature is 90 ℃, carry out the reduction reaction, react for 10 hours, filter, remove inorganic salts, filtrate Distill off methanol, extract 2-methyl-6-hydroxymethylpyridine with dichloromethane, dry with anhydrous sodium sulfate, cool to -5°C and start adding 6g of thionyl chloride dropwise, then naturally warm to room temperature for reaction 2 -3 hours, 2-methyl-6-chloromethylpyridine hydrochloride was obtained, and the total yield was 83%.

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Abstract

The invention belongs to the field of organic synthesis and specifically relates to a preparation method of 2-methyl-6-chloromethylpyridinehydrochloride. The method comprises the following steps: (1) a raw material 2-methylpyridine and an acetylating reagent are subjected to a Friedel-Crafts acylation reaction under the action of a catalyst so as to obtain 2-methyl-6-acetylpyridine; (2) the product 2-methyl-6-acetylpyridine is subjected to reduction under the action of a reducing agent to obtain 2-methyl-6-hydroxymethylpyridine; and (3) the product 2-methyl-6-hydroxymethylpyridine obtained from the step (2) undergoes a reaction under the action of a chlorination agent to obtain 2-methyl-6-chloromethylpyridinehydrochloride. The technical scheme of the invention has the beneficial effects as follows: there are few steps of acetylation reaction by the use of commonly-used chemical materials containing pyridine rings; costs are low; purity is high; yield is high; and operation is safe. The preparation method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 2-methyl-6-chloromethylpyridine hydrochloride. Background technique [0002] Pyridine ring is one of the most important heterocycles of nitrogen-containing heterocycles. From the perspective of molecular structure, the pyridine ring is equivalent to a six-membered ring in which a carbon atom on the benzene ring is replaced by a nitrogen atom. The biochemical properties of its compounds are similar to those of the benzene ring. , the pyridine ring differs greatly from the benzene ring in many properties and characteristics, especially in terms of hydrophobicity. Therefore, new pesticide compounds obtained by replacing benzene ring with pyridine ring often have higher biological activity, systemic property, selectivity and lower toxicity. One of the main reasons for the rapid development of research, development and application of various pesti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/26
CPCC07D213/26
Inventor 黄荣辉黄志强
Owner 黄荣辉