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Preparation method of 3-amino-2-hydroxypyridine

A hydroxypyridine and amino technology, applied in the field of preparation of 3-amino-2-hydroxypyridine, can solve the problems of high temperature, complicated process, easy occurrence of danger, etc., and achieve the effects of few steps, mild reaction conditions, and improved yield

Pending Publication Date: 2021-01-15
南京麦瑞米生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a preparation method of 3-amino-2-hydroxypyridine, to solve the defects in the prior art that the process is complicated and the temperature is high and danger is easy to occur

Method used

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Examples

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Effect test

preparation example Construction

[0035] A preparation method of 3-amino-2-hydroxypyridine, said method comprising the steps of:

[0036] Step 1: After mixing 2-chloropyridine and alcohol solution, add alkaline alcohol solution, and react to obtain solution 1;

[0037] Mix appropriate amount of 2-chloropyridine with alcohol solution;

[0038] After mixing evenly, add alkaline alcohol solution, adjust the temperature to 65-75°C, and react for 10-15 hours;

[0039] Wherein, the molar ratio of 2-chloropyridine to alkaline alcohol solution is 1:2-20.

[0040] The alcohol solution includes one or more of methanol, ethanol, propanol and tert-butanol.

[0041] The alkaline alcohol solution includes an alcohol solution of sodium tert-butoxide or a methanol solution of sodium methoxide.

[0042] Step 2: solution 2 is obtained after adjusting solution 1;

[0043] The obtained solution is filtered to remove the solvent to obtain a residue;

[0044] Water was added to the residue for dissolution, and an acidic substa...

Embodiment 1

[0060] Mix 1mol of 2-chloropyridine with methanol, add 2mol of sodium tert-butoxide alcohol solution, adjust the temperature to 65°C, and react for 10 hours; after the reaction, remove the solvent by filtration to obtain a residue, add Dissolve in water, and add hydrochloric acid to adjust the pH to 4, add 30v / v% hydrobromic acid to mix, keep the reaction temperature at 70°C, and stir for 7 hours; after the reaction is completed, cool and filter out the solid, add concentrated sulfuric acid to the solid, Stir to dissolve, cool to 0°C in an ice-salt bath, slowly add fuming nitric acid dropwise, and stir for half an hour after adding;

[0061] Slowly pour the reaction solution into ice and stir. After the solid precipitates, filter, wash, and dry to obtain solid 1. Put the obtained solid 1 into a single-necked bottle, then add DMF oil bath and heat to an external temperature of 60°C. Stir Make it dissolve; add 10% Pd / C under the protection of nitrogen; blow hydrogen into the hyd...

Embodiment 2

[0064]Mix 1mol of 2-chloropyridine with ethanol, add 2mol of sodium tert-butoxide alcohol solution, adjust the temperature to 70°C, and react for 10 hours; after the reaction, remove the solvent by filtration to obtain a residue, add Dissolve in water, and add dilute sulfuric acid to adjust the pH to 5, add 35v / v% hydrobromic acid to mix, keep the reaction temperature at 80°C, and stir for 10 hours; after the reaction is completed, cool and filter out the solid, add concentrated sulfuric acid to the solid , stir to dissolve, cool to 0°C in an ice-salt bath, slowly add fuming nitric acid dropwise, and stir for half an hour after adding;

[0065] Slowly pour the reaction solution into ice and stir. After the solid precipitates, filter, wash, and dry to obtain solid 1. Put the obtained solid 1 into a single-necked bottle, and then add DMF oil bath to heat to an external temperature of 65°C. Stir Make it dissolve; add 10% Pd / C under the protection of nitrogen; blow hydrogen into t...

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Abstract

The invention discloses a preparation method of 3-amino-2-hydroxy pyridine. The method comprises the following steps: mixing 2-chloropyridine with an alcoholic solution, adding an alkaline alcoholic solution, and reacting to obtain a solution I; adjusting the solution I to obtain a solution II; mixing and reacting the solution II with a hydrobromic acid solution to obtain 2-hydroxypyridine; mixing2-hydroxypyridine and concentrated sulfuric acid, adding fuming nitric acid in an environment of 0 DEG C, reacting for a period of time, and filtering to obtain a solid I; and mixing the solid I withDMF, heating to 60-70 DEG C, adding a catalyst and hydrogen, continuously reacting, and washing with diethyl ether to obtain a solid II, namely 3-amino-2-hydroxypyridine. According to the invention,the preparation method of 3-amino-2-hydroxypyridine has the advantages of simple synthesis process, fewer steps, obviously higher product yield and mild reaction conditions so as to save the production cost and achieve the industrial application value.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a preparation method of 3-amino-2-hydroxypyridine. Background technique: [0002] Pyridine is a six-membered heterocyclic compound containing a nitrogen atom, that is, one carbon of the benzene molecule is replaced by nitrogen, and it has many special medicinal effects and structural properties. Pyridine derivatives widely exist in nature, many of which have special pharmacological effects. 3-Amino-2-hydroxypyridine has the molecular formula C 5 h 6 N 2 O, with a molecular weight of 110.11 and a melting point of 170-173°C, is a kind of off-white crystal, and can also be in the state of off-white to brown powder. 3-Amino-2-hydroxypyridine is an irritant, which can be used in the pharmaceutical industry and can be used as an intermediate of anti-AIDS drugs. The raw materials for traditional 3-amino-2-hydroxypyridine synthesis are relatively expensive, the producti...

Claims

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Application Information

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IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 廖明
Owner 南京麦瑞米生物技术有限公司
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