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Synthesis method of 2-pyridine formaldoxime

A synthetic method, the technology of pyridine formaldehyde, applied in the direction of organic chemistry, etc., can solve the problems of long steps, low yield, long time consumption, etc., and achieve the effect of short production time, high yield and simple process

Inactive Publication Date: 2010-04-28
董婧
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing synthetic method of 2-pyridine formaldehyde oxime has long steps, low yield and long time-consuming

Method used

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  • Synthesis method of 2-pyridine formaldoxime
  • Synthesis method of 2-pyridine formaldoxime
  • Synthesis method of 2-pyridine formaldoxime

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] 1) Mix and heat 205 g of 2-picoline, 700 mL of glacial acetic acid, and 320 mL of 30% hydrogen peroxide, and react at 70° C. for 3.0 hours. Then add 150mL of 30% hydrogen peroxide, continue to react for 8.0 hours, distill off the liquid under reduced pressure and cool down, add 150mL of chloroform and 150mL of 15% sodium carbonate aqueous solution, stir and mix thoroughly, let stand to separate layers, and then use trichloromethane to dissolve the water layer. Methane extraction (100 mL x 3). The organic layers were combined, and after the chloroform was distilled off, the distillate at 120°C (5mmHg) was collected under reduced pressure to obtain 212g of a colorless oily liquid, with a yield of 96%.

[0015] The synthetic formula of this step is:

[0016]

[0017] 2) Add 218g (2mol) of 2-picoline nitrogen oxide into 150mL ethanol, add 273g (3mol) of sodium nitrite, and then slowly drop in 90mL of a mixture of ethanol and concentrated sulfuric acid to carry out nitro...

Embodiment 2

[0021] 1) Mix and heat 150 g of 2-picoline, 400 mL of glacial acetic acid, and 200 mL of 30% hydrogen peroxide, and react at 70° C. for 3 hours. Then add 90mL of 30% hydrogen peroxide, continue to react for 5 hours, distill off the liquid under reduced pressure and cool down, add 60mL of chloroform and 60mL of 15% aqueous sodium carbonate solution, stir and mix thoroughly, let stand to separate layers, and then use trichloromethane Methane extraction (60 mL x 3). The organic layers were combined, and after the chloroform was distilled off, the distillate at 120° C. (5 mmHg) was collected under reduced pressure to obtain 141 g of a colorless oily liquid, with a yield of 93%.

[0022] The synthetic formula of this step is:

[0023]

[0024] 2) Add 190g of 2-picoline nitrogen oxide into 120mL of ethanol, add 226g of sodium ethyl nitrite, then slowly drop in 70mL of a mixture of ethanol and concentrated sulfuric acid to carry out nitrosation reaction to obtain sodium salt, and...

Embodiment 3

[0028] 1) Mix and heat 180 g of 2-picoline, 500 mL of glacial acetic acid, and 250 mL of 30% hydrogen peroxide, and react at 70° C. for 4 hours. Then add 110mL of 30% hydrogen peroxide, continue to react for 6 hours, distill off the liquid under reduced pressure and cool down, add 100mL of chloroform and 100mL of 15% aqueous sodium carbonate solution, stir and mix thoroughly, let stand to separate layers, and then use trichloromethane to dissolve the water layer. Methane extraction (70 mL x 3). The organic layers were combined, and after the chloroform was distilled off, the distillate at 120° C. (5 mmHg) was collected under reduced pressure to obtain 168 g of a colorless oily liquid, with a yield of 91%.

[0029] The synthetic formula of this step is:

[0030]

[0031] 2) Add 200g of 2-picoline nitrogen oxide into 140mL of ethanol, add 240g of sodium nitrite, then slowly drop in 81mL of a mixture of ethanol and concentrated sulfuric acid to carry out nitrosation reaction ...

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Abstract

The invention discloses a synthesis method of 2-pyridine formaldoxime, comprising the following steps: firstly mixing 2-methyl pyridine, glacial acetic acid and hydrogen peroxide for heating, reacting at the temperature of 60-70 DEG C for 3-5 hours; secondly, adding hydrogen peroxide, continuously reacting for 5-8 hours, and then separating and purifying to obtain the nitric oxide of 2-methyl pyridine; thirdly, adding alcohol, concentrated sulfuric acid into the nitric oxide of 2-methyl pyridine to carry out nitritation reaction on sodium nitrite to obtain sodium salt, and then using concentrated hydrochloric acid to neutralize alcohol solution to pH=3-4, filtering out sodium chloride, reducing the pressure of filter liquor and then concentrating to recover alcohol so as to obtain the pralidoxime chloride crude product, then dissolving by distilled water, and carrying out active carbon decoloration and recrystallization to obtain the finished product. The invention has simple process, short production time, high yield and easy realization of industrialization.

Description

technical field [0001] The invention relates to a compound synthesis method, in particular to a synthesis method of 2-pyridine formaldehyde oxime. Background technique [0002] After organophosphate poisoning, the cholinesterase in the body is phosphorylated by the poison to form a relatively stable phosphorylated cholinesterase. Lose the ability to hydrolyze acetylcholine, resulting in symptoms of poisoning. Organophosphate antidotes widely used in clinic can reactivate poisoned phosphorylated cholinesterase, and 2-pyridine formaldehyde oxime is an important synthetic intermediate for the preparation of organophosphate antidotes. The currently reported synthetic method of 2-pyridinecarbaldehyde oxime has long steps, low yield and long time consumption. The synthesis method reported in the present invention not only significantly saves production time, but also has simple process and greatly improved yield. Contents of the invention [0003] The technical problem to be ...

Claims

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Application Information

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IPC IPC(8): C07D213/53
Inventor 董婧胡锋滕明瑜
Owner 董婧
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