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Method for synthesizing 2-methylpyridine compound

A picoline and synthetic method technology, applied in the direction of organic chemistry, can solve the problems of increased cost, low yield, and many side reactions, and achieve the effects of simple operation, reduced production cost, and simple process

Active Publication Date: 2018-07-24
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And the method for synthesizing 2-picoline mainly comprises acetaldehyde method, acetylene method, ethylene method and acrylonitrile method at present, but above four kinds of synthetic methods need the reaction environment of high temperature and high pressure and yield is low, side reaction is many, thereby greatly Increased cost in actual production

Method used

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  • Method for synthesizing 2-methylpyridine compound
  • Method for synthesizing 2-methylpyridine compound
  • Method for synthesizing 2-methylpyridine compound

Examples

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Embodiment 1

[0013]

[0014] Add triethylamine (1.0mmol, 101mg), 1a (0.5mmol, 95.5mg), elemental iodine (0.75mmol, 190.5mg) and toluene (2mL) in a 35mL Schlenk tube, and then add in O 2 Placed in an oil bath at 140°C and stirred for 12 hours under the atmosphere. The reaction was quenched by adding 50mL water, extracted with ethyl acetate (50mL×3), and then the organic phase was used with 10% Na 2 S 2 O 3 The solution and saturated brine are washed sequentially, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain the pink solid product 2-methyl-4,6-dimethylphenylpyridine 2a (49.1 mg, 72%). The characterization data of this compound are as follows: 1 H NMR(400MHz, CDCl 3 ): δ(ppm)7.92(d,J=8.0Hz,2H), 7.68(s,1H), 7.57(d,J=7.6Hz,2H), 7.33-7.24(m,5H), 2.67(s, 3H), 2.41(s, 3H), 2.40(s, 3H); 13 C NMR(100MHz, CDCl 3 )δ(ppm) 158.6, 157.5, 149.3, 138.8, 138.6, 137.1, 135.9, 129.7, 129.4, 127.0, 126.9,...

Embodiment 2

[0016] In a 35mL Schlenk tube, add triethylamine (1.0mmol, 101mg), 1a (0.5mmol, 95.5mg), ammonium iodide (0.75mmol, 168.7mg) and toluene (2mL), and then in O 2 Placed in an oil bath at 140°C and stirred for 12 hours. The reaction was quenched by adding 50 mL of water, extracted with ethyl acetate (50 mL×3), and then the organic phase was used with 10% Na 2 S 2 O 3 The solution and saturated brine are washed sequentially, and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain the target product 2a (43mg, 63%).

Embodiment 3

[0018] Add triethylamine (1.0mmol, 101mg), 1a (0.5mmol, 95.5mg), N-iodosuccinimide (0.75mmol, 108.7mg) and toluene (2mL) in a 35mL Schlenk tube, and then O 2 Placed in an oil bath at 140°C and stirred for 12 hours. The reaction was quenched by adding 50mL water, extracted with ethyl acetate (50mL×3), and then the organic phase was used with 10% Na 2 S 2 O 3 The solution and saturated brine are washed sequentially, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain the target product 2a (45.7 mg, 67%).

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Abstract

The invention discloses a method for synthesizing a 2-methylpyridine compound and belongs to the technical field of organic synthesis. According to key points of the technical scheme, the method for synthesizing the 2-methylpyridine compound in the invention comprises the following specific steps: dissolving triethylamine and oxime acetate compounds into a solvent, adding a catalyst, and reactingin an oxygen atmosphere at a temperature of 120 to 160 DEG C, thereby obtaining the 2-methylpyridine compound. The synthetic process is simple and efficient, and the 2-methylpyridine compound is directly prepared in one step by virtue of a one-pot cascade reaction without transition metal catalysis, so that waste of resources and environmental pollution caused by usage of multiple reagents in multi-step reactions and purification of an intermediate in each reaction step and the like can be avoided, the reaction conditions are mild, and the substrate application range is wide. Meanwhile, by taking the triethylamine as the raw material, the production cost is greatly reduced.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for synthesizing 2-methylpyridine compounds. Background technique [0002] Studies have shown that 2-methylpyridine is an important organic intermediate, which is mainly used for the production of long-acting sulfonamides, anti-allergic drugs chlorpheniramine, styrene butadiene latex, veterinary drugs, nitrogen fertilizer synergists, dye intermediates and herbicides Paraquat and herbicide etc. According to incomplete statistics, the domestic consumption of 2-methylpyridine is increasing at a rate of about 25% every year, so the domestic market for 2-methylpyridine has great potential. The current methods for synthesizing 2-methylpyridine mainly include acetaldehyde, acetylene, ethylene and acrylonitrile. However, the above four synthesis methods require high temperature and high pressure reaction environment, low yield and many side reactions, which grea...

Claims

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Application Information

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IPC IPC(8): C07D213/16C07D213/12C07D213/30C07D213/26C07D409/14C07D405/14
CPCC07D213/12C07D213/16C07D213/26C07D213/30C07D405/14C07D409/14
Inventor 高庆贺原焕刘兆敏吴曼曼孙佳佳周晨阳
Owner XINXIANG MEDICAL UNIV
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