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Preparation method of N-phenyl-8-aminoquinoline

A technology of aminoquinoline and phenyl, which is applied in the field of preparation of N-phenyl-8-aminoquinoline, can solve problems such as limiting industrial application, and achieve the effect of simple operation and mild reaction conditions

Inactive Publication Date: 2017-03-15
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] In summary, the existing technology can prepare diarylamine derivatives, but there are obvious shortcomings, which limit its industrial application

Method used

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  • Preparation method of N-phenyl-8-aminoquinoline
  • Preparation method of N-phenyl-8-aminoquinoline
  • Preparation method of N-phenyl-8-aminoquinoline

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment one: the preparation of a kind of N-phenyl-8-aminoquinoline derivatives, its synthetic route is:

[0024]

[0025] Embodiment 1: A kind of preparation method of N-phenyl-8-aminoquinoline derivatives is carried out according to the following steps:

[0026] (1) At room temperature, mix 8-aminoquinoline (1.0eq, 10.0mmol), benzoyl chloride (1.1eq, 11mmol), Et 3 N (1.2eq, 1.66mL), DMAP (0.3eq, 3mmol) were reacted in dichloromethane under nitrogen. After 12 hours, the reaction was quenched by adding water, extracted with dichloromethane, dried over magnesium sulfate, and concentrated by rotary evaporation. Column separation gave the target product (2.2300g, 90%).

[0027] (2) Take the target product I (1.0eq, 1mmol) of the previous step, copper acetate monohydrate (0.2eq, 0.2mmol), [PhIPh]PF 6 (2.0eq, 2mmol) into 1,2-dichloroethane, reacted in an oil bath at 80°C for 48h, and performed TLC detection. After the reaction was completed, add water to quench the r...

Embodiment 2

[0029] Embodiment two: the preparation of a kind of N-phenyl-8-aminoquinoline derivative, its synthetic route is:

[0030]

[0031] Embodiment two: the preparation of a kind of N-phenyl-8-aminoquinoline derivative, its synthetic route is:

[0032] (1) At room temperature, mix 8-aminoquinoline (1.0eq, 10.0mmol), o-methylbenzoyl chloride (1.1eq, 11mmol), Et 3 N (1.2eq, 1.66mL), DMAP (0.3eq, 0.366g) were reacted in dichloromethane under nitrogen. After 12 hours, the reaction was quenched by adding water, extracted with dichloromethane, dried over magnesium sulfate, and concentrated by rotary evaporation Column separation was performed to obtain the target product (2.2500 g, 86%).

[0033] (2) Take the target product I (1.0eq, 1.0mmol) of the previous step, copper acetate monohydrate (0.2eq, 0.2mmol), [PhIPh]PF 6 (2.0eq, 2.0mmol) into 1,2-dichloroethane, reacted in an oil bath at 80°C for 48h, and performed TLC detection. After the reaction was completed, add water to quench ...

Embodiment 3

[0035] Embodiment three: the preparation of a kind of N-phenyl-8-aminoquinoline derivative, its synthetic route is:

[0036]

[0037] Embodiment three: the preparation of a kind of N-phenyl-8-aminoquinoline derivative, its synthetic route is:

[0038] (1) At room temperature, mix 8-aminoquinoline (1.0eq, 10.0mmol), p-fluorobenzoyl chloride (1.1eq, 11mmol), Et 3 N (1.2eq, 1.66mL), DMAP (0.3eq, 3mmol) were reacted in dichloromethane under nitrogen. After 12 hours, the reaction was quenched by adding water, extracted with dichloromethane, dried over magnesium sulfate, and concentrated by rotary evaporation. Column separation gave the target product (2.3400g, 88%).

[0039] (2) Take the target product I (1.0eq, 1mmol) of the previous step, copper acetate monohydrate (0.2eq, 0.2mmol), [PhIPh]PF 6 (2.0eq, 2mmol) into 1,2-dichloroethane, reacted in an oil bath at 80°C for 48h, and performed TLC detection. After the reaction was completed, add water to quench the reaction, extract ...

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Abstract

The invention relates to a preparation method of N-phenyl-8-aminoquinoline and belongs to the technical field of organic chemical synthesis. The preparation method of the N-phenyl-8-aminoquinoline is characterized by comprising the following steps: reacting 8-aminoquinoline with acyl chloride to obtain acyl 8-aminoquinoline, and performing arylation reaction on the acyl 8-aminoquinoline and hypervalent iodonium salt on an amino group under the catalysis of copper salt to obtain an N-phenyl-N-acyl-8-aminoquinoline derivative; performing deacylation reaction on the N-phenyl-N-acyl-8-aminoquinoline to obtain the N-phenyl-8-aminoquinoline. The preparation method of the N-phenyl-8-aminoquinoline has the beneficial effects that the operating steps are simple, the reaction condition is mild, and the N-phenyl-8-aminoquinoline can serve as an excellent chelating agent and can be applied to detection of metal ion content.

Description

[0001] Technical field: [0002] The invention relates to a preparation method of N-phenyl-8-aminoquinoline, which belongs to the technical field of organic chemical synthesis. [0003] Background technique: [0004] As an important chemical raw material, diarylamine has a very wide range of uses. In the early days, diarylamines were mainly used as synthetic intermediates for dyes and medicines, as well as antioxidants for rubber and elastomers; people's attention. For example: 4-aminodiphenylamine is an important raw material for synthesizing anti-aging agents, dyes and functional polymers. From it, various important anti-aging agents such as 4010, 4010NA, 4020 and 668 can be synthesized, blue salt RT, acid red GR can be synthesized and disperse yellow GFL and other dyes, various additives in the processing of synthetic polymers, especially functional additives such as antioxidants, stabilizers and anti-degradants in the rubber industry; 4-nitrodiphenylamine can be used for ...

Claims

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Application Information

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IPC IPC(8): C07D215/40
CPCC07D215/40
Inventor 夏晓峰祝素丽
Owner JIANGNAN UNIV
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