Method used for preparing 4-aminoquinoline derivative

A technology of aminoquinoline and derivatives, which is applied in organic chemistry and other fields, can solve problems such as troublesome post-processing, cumbersome process, and complicated process, and achieve good industrial application prospects, improve reaction efficiency, and simple post-processing effects

Inactive Publication Date: 2017-06-20
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Aiming at the above technical problems in the prior art, the invention provides a method for preparing 4-aminoquinoline derivatives, the method for preparing 4-aminoquinoline derivatives will ...

Method used

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  • Method used for preparing 4-aminoquinoline derivative
  • Method used for preparing 4-aminoquinoline derivative
  • Method used for preparing 4-aminoquinoline derivative

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0020] Add 2mg of CuCl catalyst, 23mg of o-aminobenzonitrile, 22μL of phenylacetylene and 20μL of p-toluenesulfonyl azide into a 10ml reaction tube, then add 1ml of 1,4-dioxane, and replace 40mg of triethylamine with nitrogen Add dropwise to the reaction tube. The reaction mixture was heated at 70°C for 4 h, the mixture was filtered, washed three times with petroleum ether / ethyl acetate (volume ratio 5 / 1, 10 mL), the filtrate was combined and concentrated, and separated by column chromatography, the eluent was petroleum ether / ethyl acetate Ethyl acetate (volume ratio 2 / 1) was 600ml to obtain the final product N-(4-amino-3-phenyl-quinolin-2-yl)-4-methylbenzenesulfonamide with a yield of 85%.

[0021] 1 H NMR (500 MHz, CDCl 3 ) δ = 11.61 (s, 1H), 7.71 (t, J=10.0 Hz, 3H),7.51 (t, J=7.5 Hz, 1H), 7.29 (t, J=7.5 Hz, 3H), 7.21 (t, J=7.5 Hz, 1H), 7.20– 7.14 (m, 3H), 7.11 (d, J=7.5 Hz, 2H), 5.34 (s, 2H), 2.35 (s, 3H); 13 C NMR (126 MHz, CDCl 3 ) δ = 153.0, 150.8, 141.8, 141.5, 136...

Embodiment 2

[0024] Add 2 mg of CuCl catalyst, 23 mg of o-aminobenzonitrile, 39 μL of 4-methoxyphenylacetylene and 20 μL of p-toluenesulfonyl azide into a 10 ml reaction tube, then add 1 ml of 1,4-dioxane, and replace with nitrogen Add 40 mg of triethylamine dropwise to the reaction tube. The reaction mixture was heated at 70°C for 4 h, the mixture was filtered, washed three times with petroleum ether / ethyl acetate (volume ratio 5 / 1, 10 mL), the filtrate was combined and concentrated, and separated by column chromatography, the eluent was petroleum ether / ethyl acetate Ethyl acetate (volume ratio 2 / 1) 600ml to obtain the final product N-[4-amino-3-(4-methoxyphenyl)-quinolin-2-yl]-4-methylbenzenesulfonamide, The yield was 42%.

[0025] 1 H NMR (500 MHz, DMSO) δ = 11.42 (s, 1H), 8.22 (d, J=10.0 Hz, 1H),7.73 (d, J=10.0 Hz, 1H), 7.68 – 7.57 (m, 3H), 7.35 (t, J=7.5 Hz, 1H), 7.26(d, J=10.0 Hz, 2H), 7.03 (q, J=10.0 Hz, 4H), 6.69 (s, 2H), 3.81 (s, 3H), 2.31(s, 3H); 13 C NMR (126 MHz, DMSO) Δ =...

Embodiment 3

[0027] Add 2 mg of CuCl catalyst, 23 mg of o-aminobenzonitrile, 25 μL of 3-methylphenylacetylene and 20 μL of p-toluenesulfonyl azide into a 10 ml reaction tube, then add 1 ml of 1,4-dioxane, and replace with nitrogen 40 mg of triethylamine was added dropwise into the reaction tube. The reaction mixture was heated at 70°C for 4h, the mixture was filtered, washed three times with petroleum ether / ethyl acetate (volume ratio 5 / 1, 10mL), the filtrate was combined and concentrated, and separated by column chromatography, the eluent was petroleum ether / ethyl acetate Ethyl acetate (volume ratio 2 / 1) was 600ml to obtain the final product N-(4-amino-3-m-tolyl-quinolin-2-yl)-4-methylbenzenesulfonamide with a yield of 68%.

[0028] 1 H NMR (500 MHz, CDCl 3) δ = 11.72 (s, 1H), 7.73 (d, J=10.0 Hz, 2H),7.69 (d, J=5.0 Hz, 1H), 7.56 (t, J=7.5 Hz, 1H), 7.32 (d, J=10.0 Hz, 1H), 7.26– 7.17 (m, 4H), 7.09 (d, J=5.0 Hz, 1H), 6.95 (s, 2H), 5.24 (s, 2H), 2.37 (s,3H), 2.29 (s, 3H); 13 C NMR (126 ...

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Abstract

The invention discloses a method used for preparing a 4-aminoquinoline derivative. According to the method, an acuprous catalyst, an additive, and o-aminobenzontrile are delivered into a reaction container, wherein the additive is one ingredient selected from triethylamine, tetramethyl ethylenediamine, 1,8-diazabicyclo undec-7-ene, potassium carbonate, or cesium carbonate at will; an organic solvent is added; an alkyne-terminated compound and p-toluenesulfonyl azide are introduced into the reaction container; an obtained mixture is subjected to heating reaction for 3h to 6h at a temperature ranging from room temperature to 100 DEG C, wherein reaction process is monitoring via thin-layer chromatography, and optimal reaction conditions are obtained via selection; after reaction, an obtained mixture is filtered, obtained filter cake is washed, obtained filtrate is mixed, and is subjected to condensation and column chromatography separation so as to obtain the 4-aminoquinoline derivative. One-pot method is adopted to prepare the 4-aminoquinoline derivative, reaction efficiency is increased greatly, post-treatment is simple; and industrialized application prospect is promising.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a 4-aminoquinoline derivative, in particular to a method for preparing a 4-aminoquinoline derivative. Background technique [0002] Quinoline exists widely in the biological world, and quinoline can be extracted from coal tar wash oil or naphthalene oil. Quinoline is a naphthalene-like nitrogen-containing heterocyclic compound. That is, the N atom at the 1-position replaces CH, so it is also called azanaphthalene, and quinoline has important applications in the medicine and dye industries. At present, there are many synthetic routes of quinoline reported in the literature, and the traditional industrial production route is coal tar extraction. Due to limited resources, complex extraction equipment, and the limited variety of quinoline and its homologues in coal tar, it is impossible to obtain the desired compound containing quinoline rings, so chemical synthesis methods emerged ...

Claims

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Application Information

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IPC IPC(8): C07D215/42
CPCC07D215/42
Inventor 易封萍张松幸易维银张丽荣樊燕霞黄颖孙启辉
Owner SHANGHAI INST OF TECH
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