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Synthetic method of chloromethylpyridine or pyridine derivative hydrochloride of chloromethylpyridine

A technology of chloromethylpyridine and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of troublesome recovery of precious metals, high pressure on cost and price, and dangerous operation of feeding materials, and achieve the effects of low cost, few reaction steps, and safe operation

Active Publication Date: 2012-07-25
JIANGSU ZHONGBANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, using methyllithium, methyl iodide, etc. as raw materials has high pressure on cost and price, and it is troublesome to recover precious metals and iodine elements; using dimethyl sulfate is highly toxic and dangerous for feeding operations.

Method used

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  • Synthetic method of chloromethylpyridine or pyridine derivative hydrochloride of chloromethylpyridine
  • Synthetic method of chloromethylpyridine or pyridine derivative hydrochloride of chloromethylpyridine
  • Synthetic method of chloromethylpyridine or pyridine derivative hydrochloride of chloromethylpyridine

Examples

Experimental program
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Effect test

Embodiment 1

[0020] In a 500ml flask, add 9.2g of 4-methoxy-3,5-lutidine nitrogen oxide, 60ml of methanol, add 0.8g of aluminum trichloride, cool to below 0°C and start adding ethyl chloroformate dropwise After the addition of 7.8g of ester, the temperature was raised to a reaction temperature of 45°C to 95°C, and the reaction was carried out under reflux for 4 to 6 hours. Sampling and analysis was carried out until the raw material 4-methoxy-3,5-lutidine nitrogen oxide disappeared. until reduced; add 6.75g of sodium tetrahydroborate to the system, and the reaction temperature is 55-65°C for reduction. React for 5 hours, filter, filter out inorganic salts, distill the filtrate to remove methanol, extract 2-hydroxymethyl-4-methoxy-3,5-lutidine with dichloromethane, dry the dichloromethane phase, and cool 14g of thionyl chloride was added dropwise at -10°C, and then the temperature was naturally raised to room temperature for 2-3 hours to obtain 2-chloromethyl-4-methoxy-3,5-lutidine hydrochl...

Embodiment 2

[0022] In a 500ml flask, add 10g of 4-nitro-3,5-lutidine nitrogen oxide, 60ml of methanol, add 0.5g of magnesium oxide, cool to below 0°C and start adding 6.2g of acetic anhydride dropwise, dropwise After completion, raise the temperature to a reaction temperature of 45°C to 95°C, reflux for 4 to 6 hours, and take samples for analysis until the raw material 4-nitro-3,5-lutidine nitrogen oxide does not decrease; add 6.75g of lithium tetrahydrogen aluminum, the reaction temperature is 85-95 ° C, for reduction. React for 7 hours, filter, filter out inorganic salts, distill the filtrate to remove methanol, extract 2-hydroxymethyl-4-nitro-3,5-lutidine with dichloromethane, dry the dichloromethane phase, and cool to 18g of phosphorus trichloride was added dropwise at -20°C, and then the temperature was naturally raised to room temperature for 2-3 hours to obtain 2-chloromethyl-4-nitro-3,5-lutidine hydrochloride, which was weighed 11.9 g of off-white solid was obtained, and analyzed...

Embodiment 3

[0024] In a 500ml flask, add 7.3g of 3,5-lutidine nitrogen oxide, 60ml of methanol, add 4.0g of zinc chloride, cool to below 0°C and start adding chloroacetyl (CH 3 COCl) 9.3g, after the dropwise addition is completed, the temperature is raised to a reaction temperature of 45°C to 95°C, and the reflux reaction is carried out for 4 to 6 hours, and sampling and analysis are carried out until the raw material 3,5-lutidine nitrogen oxide does not decrease; Add 6.75gFe / 10mlAcOH to it, and the reaction temperature is 45-55°C for reduction. React for 12 hours, filter out inorganic salts, distill off methanol, extract 2-hydroxymethyl-3,5-lutidine with dichloromethane, dry the dichloromethane phase, cool to -5°C and start feeding 8.4g Chlorine, and then naturally warmed up to room temperature for 1 to 2 hours to obtain 2-chloromethyl-3,5-lutidine hydrochloride. Weighed 9.1 g of white solid, analyzed by HPLC: the purity was 98.45%. The total yield of the three-step reaction is 80.5%. ...

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Abstract

The invention discloses a synthetic method of chloromethylpyridine or pyridine derivative hydrochloride of the chloromethylpyridine. The synthetic method is characterized in that according to the method, the positioning effect of substitutional groups is used for carrying out chloromethylation reaction, raw materials of pyridine or pyridine derivatives are subjected to Friedel-Crafts acylation reaction under the catalyst effect, No.2 sites or No.6 sites of the pyridine or the pyridine derivatives take electrophilic substitution reaction, then, hydroxymethylpyridine or hydroxymethylpyridine derivatives are obtained through reduction reaction, next, the chloromethylpyridine or the pyridine derivative hydrochloride is obtained through chlorination reaction, and the structure of the obtained product is shown as the accompanying drawing. The method has the advantages that the reaction steps are few, the cost is low, the purity is high, the yield is high, the operation is safe, and the method is suitable for large-scale industrial production.

Description

Technical field: [0001] The invention belongs to the field of chemistry, and specifically relates to a method for synthesizing chloromethylpyridine or its pyridine derivative hydrochloride. Chloromethylpyridine and pyridine derivative hydrochloride are various pesticides, pharmaceutical intermediates, pesticides, An important chemical raw material for herbicides and fungicides. The method directly generates 2-chloromethylpyridine and pyridine derivatives from pyridine or its pyridine derivatives. Background technique: [0002] Chloromethylpyridine and pyridine derivatives hydrochloride are important chemical raw materials for various pesticides, pharmaceutical intermediates, insecticides, herbicides, and fungicides. At present, pyridine and pyridine derivatives are directly methylated, using expensive noble metal chemical raw materials such as methyllithium and methyl iodide, or directly cyclized to have a methyl group at the 2-position, and then chlorine gas is passed to ca...

Claims

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Application Information

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IPC IPC(8): C07D213/68C07D213/61C07D213/26
Inventor 秦必政薛谊徐强李维思赵华阳周颖钱勇肖云
Owner JIANGSU ZHONGBANG PHARMA
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