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Method for efficiently synthesizing quinoline

A derivative, quinoline technology, applied in the field of quinoline derivatives, can solve the problems of limited quinoline derivatives, high reaction temperature, harsh reaction conditions, etc., and achieve the effects of easy separation and purification, single product, and simple operation

Inactive Publication Date: 2014-11-19
NANYANG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] There are many disadvantages in the current synthetic method: the main reason is that the reaction conditions are harsh, the reaction temperature is high, some require high temperature and high pressure, separation is difficult, and the substrate restriction of the reaction is strong, so the quinoline derivatives of the synthetic substituent are very limited
In addition, in the process of using metal catalysis, the activity of the catalyst is limited. These shortcomings make the operation of the preparation process more difficult, endanger the health of operators, and cause serious environmental pollution.

Method used

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  • Method for efficiently synthesizing quinoline
  • Method for efficiently synthesizing quinoline
  • Method for efficiently synthesizing quinoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of 2,4-diphenylquinoline: Add 0.5 mmol (46.5 mg) of aniline, 0.005 mmol (1.29 mg) of catalyst AgOTf, 0.5 mmol (104 mg) of 1,3-diphenylpropenone into the reaction vessel, Toluene 2mL. at 110 o React in a C oil bath for 10 hours, cool to room temperature, extract the product with ethyl acetate, concentrate under reduced pressure, and purify the product by column chromatography to obtain a white solid product with a yield of 96%. 1 H NMR (500 MHz, CDCl 3 ) ppm: 8.43 (d, J = 8.0 Hz, 1H), 8.34 (d, J = 8.0 Hz, 2H), 8.00 (d, J = 8.5 Hz, 1H), 7.92 (s, 1H), 7.80 (t, 1H), 7.51 - 7.64 (m, 9H); 13 C NMR (500 MHz, CDCl 3 ): 156.90, 149.23, 149.05, 139.77, 138.56, 130.35, 129.70, 129.60, 129.50, 128.96, 128.52, 127.75, 125.92, 125.75, 119.39; 21 h 15 N: [M+ ], 281.1207; Found: 281.1204.

Embodiment 2

[0029] Preparation of 4-phenylquinoline: Add 0.5 mmol (46.5 mg) of aniline, 0.005 mmol (1.29 mg) of catalyst AgOTf, 0.5 mmol (66 mg) of 3-phenylacrolein, and 2 mL of toluene into a reaction vessel. at 110 o React in a C oil bath for 10 hours, cool to room temperature, extract the product with ethyl acetate, concentrate under reduced pressure, and purify the product by column chromatography to obtain a white solid product with a yield of 90%.

Embodiment 3

[0031] Preparation of 4-phenyl-2-p-tolylquinoline: 0.5 mmol (46.5 mg) of aniline, 0.005 mmol (1.29 mg) of catalyst AgOTf, 3-phenyl-1-p-tolyl-?? Acrylketone 0.5 mmol (11.1 mg), toluene 2mL. at 100 o React in a C oil bath for 7 hours, cool to room temperature, extract the product with ethyl acetate, concentrate under reduced pressure, and purify the product by column chromatography to obtain a white solid product with a yield of 89%. 1 H NMR (500 MHz, CDCl 3 ) ppm: 8.36 (d, J =8.0 Hz, 1H), 8.25 (d, J = 8.0 Hz, 2H), 7.95 - 7.93 (d, J = 8.0 Hz, 1H), 7.85 (s, 1H), 7.81 - 7.74 (m, 1H), 7.61 - 7.52 (m, 6H), 7.38 - 7.36 (d, J = 8.0 Hz, 2H), 2.46 (s, 3H); 13 C NMR (500 MHz, CDCl 3 ): 156.9, 149.2, 148.6, 139.4, 138.4, 136.7, 120.2, 129.6, 129.5, 128.5, 128.2, 127.4, 126.1, 125.6, 125.5, 119.1, 21.5) C CalMS for E 22 h 17 N: [M + ], 295.1369; Found: 295.1365.

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Abstract

The invention provides a method for efficiently synthesizing quinoline. The quinoline is synthesized by phenylamine and olefin ketone with substituents catalyzed by silver trifluoromethanesulfonate, as well as an olefine aldehyde derivative. The method is simple to operate, is applicable to many functional groups, has high yield and a single product, facilitates separation and purification, and is safe, cheap and low in pollution.

Description

technical field [0001] The present invention relates to quinoline derivatives, in particular to a method for efficiently synthesizing quinoline derivatives, which is a method for synthesizing quinoline derivatives using silver trifluoromethanesulfonate to catalyze substituent aniline and enone or enaldehyde derivatives method. Background technique [0002] As an important N-heterocyclic fine chemical raw material, quinoline compounds are widely used in medicine, pesticides, spices, food, dyes, synthetic feed additives, and plant auxins. Quinoline compounds widely exist in nature, but the separation and purification from nature not only requires many steps, complicated separation devices, high energy consumption, high process cost, and serious environmental pollution, for example: quinoline can be extracted from coal tar washing oil or Extracted from naphthalene oil. The naphthalene oil fraction and the washing oil fraction are washed with dilute sulfuric acid to obtain...

Claims

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Application Information

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IPC IPC(8): C07D215/06C07D215/14C07D215/18
CPCC07D215/06C07D215/14C07D215/18
Inventor 张旭徐学锋于林涛赵强王志强毛武涛
Owner NANYANG NORMAL UNIV
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