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A kind of preparation method of 2-methyl-4-aminoquinoline

An aminoquinoline, aminated quinoline technology, applied in the direction of organic chemistry and the like, can solve the problem of high requirements for reaction equipment, and achieve the effects of solving the difficulty of the reaction, reducing the production cost, and high purity and yield

Active Publication Date: 2021-02-12
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

Method used

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  • A kind of preparation method of 2-methyl-4-aminoquinoline
  • A kind of preparation method of 2-methyl-4-aminoquinoline
  • A kind of preparation method of 2-methyl-4-aminoquinoline

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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 present invention relates to a kind of preparation method of 2-methyl-4-aminoquinoline, comprising the steps of: (1) dissolving 2-methyl-4-chloroquinoline in a solvent, then adding substituted benzylamine or benzylamine and Amination reaction of alkali occurs to obtain 2-methyl-4-aminated quinoline; (2) 2-methyl-4-aminated quinoline obtains described 2-methyl-4-aminated quinoline through debenzylation reaction aminoquinoline. The preparation method of 2-methyl-4-aminoquinoline of the present invention takes 2-methyl-4-chloroquinoline as a starting material, adds substituted benzylamine or benzylamine to carry out ammoniation reaction under alkaline conditions, and undergoes debenzylation The target product is obtained after the reaction. The method of the invention requires low preparation conditions, solves the problem of high difficulty in the reaction of synthesizing amino compounds from chlorinated compounds, and the obtained product has high purity and yield, reduces production costs, and has popularization value.

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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Patent Type & Authority Patents(China)
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