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Method for preparing 2-amino-3-hydroxymethylpyridine

A technology of hydroxymethylpyridine and aminopyridine, which is applied in the field of preparation of 2-amino-3-hydroxymethylpyridine, can solve the problems of expensive excipients, high reaction temperature, large production sewage, etc., and achieve low raw material cost , high yield and easy operation

Inactive Publication Date: 2018-10-19
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The purpose of the present invention is to: aim at the above-mentioned existing problems, provide a kind of preparation method of 2-amino-3-hydroxymethylpyridine, this method overcomes the high reaction temperature existing in the prior art, the production sewage discharge is big, the excipient price is expensive and technical problems such as low yield

Method used

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  • Method for preparing 2-amino-3-hydroxymethylpyridine
  • Method for preparing 2-amino-3-hydroxymethylpyridine
  • Method for preparing 2-amino-3-hydroxymethylpyridine

Examples

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Effect test

Embodiment 1

[0033] A kind of preparation method of 2-amino-3-hydroxymethylpyridine:

[0034] S1. At room temperature, add dichloromethane (900g) into a 2L three-necked flask, add 2-aminopyridine (135g, 1.0eq) and triethylamine (174g, 1.2eq) in sequence, cool to 10-20°C, Pivaloyl chloride (189g, 1.1eq) was added dropwise. After the dropwise addition, the system was warmed up to 20-25°C and reacted for 2-3h;

[0035] After the reaction was completed, water was added to the reaction system, and after stirring for 0.5 h, the organic phase was separated, the aqueous phase was extracted with dichloromethane (500 g), and the organic phase was concentrated to dryness. At 0°C, petroleum ether (800 g) was directly added, stirred for 2 h, and suction filtered to obtain 2-pivalamidopyridine with a yield of 83%. NMR detection: 1H-NMR (400MHz, CDCl 3 ):δ8.23(2H,m,J=8Hz),8.03(1H,s),7.65(1H,t,J=4Hz),7.00(1H,t,J=4Hz),1.30(9H,s) .

[0036] S2. Under the protection of nitrogen, the above-mentioned 2-piv...

Embodiment 2

[0041] A kind of preparation method of 2-amino-3-hydroxymethylpyridine:

[0042] S1. At room temperature, add dichloromethane (945g) into a 2L three-necked flask, add 2-aminopyridine (135g, 1.0eq) and triethylamine (188g, 1.3eq) in sequence, cool to 10-20°C, Pivaloyl chloride (198g, 1.15eq) was added dropwise. After the dropwise addition, the system was warmed to 20-25°C and reacted for 2-3h;

[0043] After the reaction was completed, water was added to the reaction system, and after stirring for 0.5 h, the organic phase was separated, the aqueous phase was extracted with dichloromethane (500 g), and the organic phase was concentrated to dryness. At 0°C, petroleum ether (800 g) was directly added, stirred for 2 h, and suction filtered to obtain 2-pivalamidopyridine with a yield of 84%. NMR detection: 1H-NMR (400MHz, CDCl 3 ):δ8.23(2H,m,J=8Hz),8.03(1H,s),7.65(1H,t,J=4Hz),7.00(1H,t,J=4Hz),1.30(9H,s) .

[0044] S2. Under the protection of nitrogen, the above-mentioned 2-pivalam...

Embodiment 3

[0049] A kind of preparation method of 2-amino-3-hydroxymethylpyridine:

[0050] S1. At room temperature, add dichloromethane (900g) into a 2L three-necked flask, add 2-aminopyridine (135g, 1.0eq) and triethylamine (174g, 1.2eq) in sequence, cool down to 15°C, add dropwise Pivaloyl chloride (189g, 1.1eq), after the dropwise addition, the system was warmed up to 20-25°C, and reacted for 2-3h;

[0051] After the reaction was completed, water was added to the reaction system, and after stirring for 0.5 h, the organic phase was separated, the aqueous phase was extracted with dichloromethane (500 g), and the organic phase was concentrated to dryness. At 0°C, petroleum ether (800 g) was directly added, stirred for 2 h, and suction filtered to obtain 2-pivalamidopyridine with a yield of 80.8%. NMR detection: 1H-NMR (400MHz, CDCl 3 ):δ8.23(2H,m,J=8Hz),8.03(1H,s),7.65(1H,t,J=4Hz),7.00(1H,t,J=4Hz),1.30(9H,s) .

[0052] S2. Under the protection of nitrogen, the above-mentioned 2-piva...

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Abstract

The invention discloses a method for preparing 2-amino-3-hydroxymethylpyridine, and belongs to the field of chemical synthesis. 2-aminopyridine and pivaloyl chloride are used as initial reactants to form intermediate product 2-pivalamidopyridine under the action of triethylamine, after hydrogen extraction by use of n-butyllithium, dimethylformamide is added for hydroformylation, and target product2-amino-3-hydroxymethylpyridine can be obtained by reduction with sodium borohydride. Raw materials used in the method are low in cost, and the method is simple in operation, short in synthesis process, mild in reaction conditions, high in yield, and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of 2-amino-3-hydroxymethylpyridine. Background technique [0002] Since the discovery of the first quinolone drug "nalidixic acid" in the early 1960s, quinolone drugs have developed into a wide variety of anti-infective drugs. Quinolones are divided into four generations, and the third generation is currently used more clinically, such as norfloxacin, ofloxacin and ciprofloxacin and other antibiotics. This type of antibiotic has a broad antibacterial spectrum, strong efficacy against Gram-negative bacteria, low toxicity to animals and humans, and specific inhibition of bacterial DNA synthesis. And 2-amino-3-hydroxymethylpyridine is the most important intermediate in the synthesis of naphthyridones, and there are many synthetic methods. [0003] Allen A.Thomas et al reported in the literature "Bioorganic & Medicinal Chemistry Letters, 2008...

Claims

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Application Information

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IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 罗建业李宏强郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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