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Preparation method of 2-methyl-4-aminoquinoline

A technology of aminoquinoline and aminated quinoline, which is applied in the direction of organic chemistry, can solve the problem of high requirements for reaction equipment, achieve the effect of solving difficult reaction, reducing production cost, high purity and yield

Active Publication Date: 2020-04-07
武汉智顿科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The existing method for synthesizing 2-methyl-4-aminoquinoline is obtained by direct amination of 2-methyl-4-chloroquinoline. This method requires noble metal catalysts and high pressure conditions, and has high requirements for reaction equipment. Another report Using 2-hydroxy-4-chloroquinoline as a raw material to react with N,N-diethylchloroformamide to obtain an ester, and react with ammonia to obtain a product. Although this synthetic route avoids noble metal catalysts, it still requires high pressure conditions

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  • Preparation method of 2-methyl-4-aminoquinoline
  • Preparation method of 2-methyl-4-aminoquinoline
  • Preparation method of 2-methyl-4-aminoquinoline

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Experimental program
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Effect test

Embodiment 1

[0033] A kind of preparation method of 2-methyl-4-aminoquinoline of the present embodiment, comprises the steps:

[0034] (1) Dissolve 2-methyl-4-chloroquinoline (5.31g, 0.03mol) in 30mL N,N-dimethylformamide, then add p-oxybenzylamine (4.52g, 0.033mol), three Ethylamine (3.10g, 0.03mol), heat up to 120°C for 4 hours, cool down, pour the reaction solution into water, a off-white precipitate precipitates, filter with suction, wash the filter cake with water three times, and dry the filter cake to obtain the product 2-methyl -4-N-(4-methoxy)benzylaminoquinoline 7.19g, yield 86.1%, HPLC purity 96.2%;

[0035] (2) Dissolve 2-methyl-4-N-(4-methoxy)benzylaminoquinoline (5.6g, 0.02mol) in methanol, add 0.5g palladium carbon, feed hydrogen, heat up to 50°C, Reacted for 6h, cooled, filtered, and spin-dried to obtain 2.82 g of the product 2-methyl-4-aminoquinoline, with a yield of 89.6% (with 2-methyl-4-N-(4-methoxy) benzylaminoquinoline Calculated based on the amount of phylloline su...

Embodiment 2

[0037] A kind of preparation method of 2-methyl-4-aminoquinoline of the present embodiment, comprises the steps:

[0038] (1) Dissolve 2-methyl-4-chloroquinoline (5.31g, 0.03mol) in 30mL dimethyl sulfoxide, then add p-oxybenzylamine (13.56g, 0.1mol), N,N-di Isopropylethylamine (3.87g, 0.03mol), heat up to 140°C, react for 2 hours, cool down, pour the reaction solution into water, a off-white precipitate precipitates, filter with suction, wash the filter cake with water three times, and dry the filter cake to obtain the product 2-Methyl-4-N-(4-methoxy)benzylaminoquinoline 6.84g, yield 85.3%, HPLC purity 97.4%;

[0039] (2) Dissolve 2-methyl-4-N-(4-methoxy)benzylaminoquinoline (5.6g, 0.02mol) in formic acid, add 0.5g of palladium carbon, feed hydrogen, and heat up to 50°C , reacted for 6h, cooled, filtered, and spin-dried to obtain 2.76g of product 2-methyl-4-aminoquinoline, with a yield of 88.7% (based on 2-methyl-4-N-(4-methoxy)benzyl The amount of aminoquinoline substance i...

Embodiment 3

[0041] A kind of preparation method of 2-methyl-4-aminoquinoline of the present embodiment, comprises the steps:

[0042] (1) Dissolve 2-methyl-4-chloroquinoline (5.31g, 0.03mol) in 30mL N,N-dimethylformamide, then add 2,4-dimethoxybenzylamine (5.01g, 0.033 mol), potassium carbonate (4.14g, 0.03mol), heated up at 120°C and reacted for 4h, cooled down, poured the reaction solution into water, a off-white precipitate precipitated out, filtered with suction, washed the filter cake with water three times, and dried the filter cake to obtain the product 2- Methyl-4-N-(2,4-dimethoxy)benzylaminoquinoline 7.11g, yield 86%, HPLC purity 96.5%;

[0043] (2) Dissolve 2-methyl-4-N-(2,4-dimethoxy)benzylaminoquinoline (6.16g, 0.02mol) in acetonitrile, add cerium ammonium nitrate (10.96g, 0.02mol) Raise the temperature to 40°C, react for 5 hours, cool down, filter, spin dry, add water and dichloromethane for extraction, extract three times and combine the organic phases, dry, and precipitate...

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Abstract

The invention relates to a preparation method of 2-methyl-4-aminoquinoline. The method comprises the following steps: (1) dissolving 2-methyl-4-chloroquinoline in a solvent, adding substituted benzylamine or benzylamine and an alkali, and carrying out an ammoniation reaction in order to obtain 2-methyl-4-aminoquinoline; and (2) carrying out a debenzylation reaction on the 2-methyl-4-aminoquinolineto obtain the 2-methyl-4-aminoquinoline. The preparation method of the 2-methyl-4-aminoquinoline takes the 2-methyl-4-chloroquinoline as a starting material, the substituted benzylamine or benzylamine is added, the ammoniation reaction is carried out under an alkaline condition, and the debenzylation reaction is carried out to obtain the target product. The method has characteristics of low preparation condition requirement, solving of the problem of high reaction difficulty in the synthesis of amino compounds from chlorides, high purity and high yield of the obtained product, production costreduction, and promotion values.

Description

technical field [0001] The invention belongs to the technical field of chemical industry and medicine, and in particular relates to a preparation method of 2-methyl-4-aminoquinoline. Background technique [0002] Due to their good pharmacological activity, quinoline compounds are widely used as intermediates of anti-tumor, anti-inflammatory, anti-bacterial, cardiovascular disease and other drugs. 2-Methyl-4-aminoquinoline has certain antitumor activity and strong anti-inflammatory and bactericidal activity, and is the main functional group of the anti-inflammatory drug dequalinium chloride. Therefore, the synthesis of 2-methyl-4-aminoquinoline has attracted much attention, and the molecular formula of 2-methyl-4-aminoquinoline is as follows: [0003] The existing method for synthesizing 2-methyl-4-aminoquinoline is obtained by direct amination of 2-methyl-4-chloroquinoline. This method requires noble metal catalysts and high pressure conditions, and has high requirements ...

Claims

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Application Information

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IPC IPC(8): C07D215/42
CPCC07D215/42
Inventor 李亚平谢洪磊张瑞鹏张艺兴
Owner 武汉智顿科技发展有限公司