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4-aminopyridine preparation method

A technology of aminopyridine and isonicotinamide, which is applied in the field of preparation of 4-aminopyridine, can solve the problem that the yield of Hofmann degradation reaction is not very high, and achieve the effects of low price, mild reaction conditions and cost reduction

Inactive Publication Date: 2006-07-26
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the price of iodobenzene is relatively expensive, and the yield of Hofmann degradation reaction is not very high

Method used

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  • 4-aminopyridine preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0016] (1) Weigh 2.54g (0.01mol) of commercially available analytically pure iodine and put it into a 500ml three-necked bottle, add 18g (1mol) of deionized water to dissolve it, and then put the three-necked bottle into ice at 0-5°C In the water bath, add 22g (0.55mol) of commercially available analytically pure sodium hydroxide, add 90g (5mol) of deionized water under stirring conditions to make it dissolve, then slowly add dropwise commercially available analytically pure bromine 39.95g (0.25mol ), after fully stirring evenly, it is the prepared catalyst.

[0017] (2) Weigh 26.87g (0.22mol) of commercially available chemically pure isonicotinamide, add it to the above-mentioned three-necked flask containing the prepared catalyst, keep the reaction temperature at 0-5°C, stir for 45min, then slowly increase Reaction temperature to 80°C, and keep it for 50min, then, add 1N dilute hydrochloric acid solution to strong acidity (pH value is 1~2), cool down to room temperature unde...

Embodiment 2

[0020] (1) Weigh 1.66g (0.01mol) of commercially available analytically pure potassium iodide into a 500ml three-necked bottle, add 27g (1.5mol) of deionized water to dissolve it, and then put the three-necked bottle into a 0-5°C In the ice-water bath, add commercially available analytically pure potassium hydroxide 28.06g (0.50mol), add deionized water 72g (4mol) under stirring condition and make it dissolve, then slowly add dropwise commercially available analytically pure bromine 47.94g ( 0.30mol), after fully stirring evenly, it is the prepared catalyst.

[0021] (2) Weigh 30.53g (0.25mol) of commercially available chemically pure isonicotinamide, add it to the three-necked flask containing the prepared catalyst, keep the reaction temperature at 0-5°C, stir for 50min, and then slowly increase Reaction temperature to 75°C, and keep it for 55min, then, add 1N dilute hydrochloric acid solution to strong acidity (pH value is 1~2), cool down to room temperature while stirring, ...

Embodiment 3

[0024] (1) Take commercially available analytically pure sodium iodide 1.50g (0.01mol) and put it into a 500ml there-necked bottle, add 18g (1mol) of deionized water and 22ml of deionized water to dissolve it, and then put the there-necked bottle into Add 28g (0.70mol) of commercially available analytically pure sodium hydroxide to an ice-water bath at 0-5°C, add 72g (4mol) of deionized water under stirring conditions to dissolve it, then slowly add dropwise commercially available analytically pure sodium hydroxide 43.15g (0.27mol) of bromine, after fully stirring evenly, is the prepared catalyst.

[0025] (2) Weigh 25.65g (0.21mol) of commercially available chemically pure isonicotinamide, add it to the three-necked flask containing the prepared catalyst, keep the reaction temperature at 0-5°C, stir for 45min, and then slowly increase Reaction temperature to 70°C, and keep it for 60min, then, add 1N dilute hydrochloric acid solution to strong acidity (pH value is 1~2), cool d...

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Abstract

The invention relates to a Method for preparation of 4-aminopyridine. This invention is based on the Hofmann degradation rezction of iosniacinamide to prepare 4-aminopyridine, making catalyzer by low-cost iodine or alkali metal iodide, sodium hydroxide orporassium hudroxide and bromine according to certain proportion and condition. The productivity of Hofmann degradation rezction of iosniacinamide is improved above 90%, the purity of 4-aminopyridine is higher than 99%. This can not only improve the productivity of 4-aminopyridine which is made by isonicotinic acid, but also reduce the cost of catalyzer greatly. It has important application-value to prepare 4-aminopyridine which is made by isonicotinic acid.

Description

Technical field: [0001] The invention relates to a preparation method of 4-aminopyridine. Background technique: [0002] 4-aminopyridine (also known as p-aminopyridine) is an important intermediate for the synthesis of medicines, pesticides, and dyes, and can also be used as a food additive and a raw material for efficient acylation catalyst 4-dimethylaminopyridine. [0003] At present, there are two main methods for synthesizing 4-aminopyridine. One is to use pyridine as a starting material, and then oxidize it to obtain pyridine nitrogen oxide, then nitrate it with mixed acid to produce 4-nitropyridine nitrogen oxide, and finally reduce it to obtain 4 - aminopyridine. The synthesis route of this method is relatively long, and a large amount of strong acid is used during the nitration of mixed acid, which is relatively polluting to the environment (Progress in the synthesis technology of 4-aminopyridine and its application, Modern Chemical Industry, 2004, Vol.24(5), pp.16-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
Inventor 季生福胡林华李成岳
Owner BEIJING UNIV OF CHEM TECH
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