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Preparation method of 2-methyl-6-(chloromethyl) pyridine hydrochloride

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 high raw material cost and long route, and achieve low cost, The effect of high yield and high purity

Inactive Publication Date: 2015-12-30
JIANGSU MENGDE NEW MATERIALS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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-(chloromethyl) pyridine hydrochloride

Examples

Experimental program
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Effect test

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 After -3 hours, 2-methyl-6-chloromethylpyridine hydrochloride was obtained with a total yield of 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 ° C, 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 After -3 hours, 2-methyl-6-chloromethylpyridine hydrochloride was obtained with a total yield of 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 reduction reaction, react for 10 hours, filter, remove inorganic salts, filtrate Distill methanol off, 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 After -3 hours, 2-methyl-6-chloromethylpyridine hydrochloride was obtained with a total yield of 83%.

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Abstract

The invention belongs to the field of organic synthesis and particularly relates to a preparation method of 2-methyl-6-(chloromethyl) pyridine hydrochloride. The preparation method comprises the following steps: (1), 2-methylpyridine as a raw material and an acylation agent have a Friedel-Crafts reaction under the action of a catalyst, and 2-methyl-6-acetylpyridine is obtained; (2), the product 2-methyl-6-acetylpyridine obtained in the step (1) is reduced to 2-methyl-6-hydroxymethylpyridine under the action of a reducing agent; (3), 2-methyl-6-(chloromethyl) pyridine hydrochloride is obtained from the product 2-methyl-6-hydroxymethylpyridineobtained in the step (2) under the action of a chlorination agent. With adoption of the technical scheme, the preparation method has the benefits as follows: commonly used chemical raw materials containing pyridine rings are adopted for acetylation reaction, so that the steps are few, the cost is low, the purity and the yield are high, the operation is safe, and the method is applicable to 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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IPC IPC(8): C07D213/26
CPCC07D213/26
Inventor 杭冬良
Owner JIANGSU MENGDE NEW MATERIALS TECH CO LTD
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