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A method for efficiently synthesizing quinoline derivatives

A derivative and 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: 2015-11-11
NANYANG NORMAL UNIV
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  • Summary
  • 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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  • A method for efficiently synthesizing quinoline derivatives
  • A method for efficiently synthesizing quinoline derivatives
  • A method for efficiently synthesizing quinoline derivatives

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 AgOTf, 0.5 mmol (104 mg) of 1,3-diphenylpropenone, and toluene into the reaction vessel. 2mL. At 110 o C was reacted in an oil bath for 10 hours, cooled to room temperature, the product was extracted with ethyl acetate, and concentrated under reduced pressure. The product was purified by column chromatography to obtain a white solid product with a yield of 96%. 1 HNMR(500MHz, CDCl 3 )ppm:8.43(d, J =8.0Hz,1H),8.34(d, J =8.0Hz,2H),8.00(d, J =8.5Hz,1H),7.92(s,1H),7.80(t,1H),7.51-7.64(m,9H); 13 CNMR(500MHz, CDCl 3 ): 156.90,149.23,149.05,139.77,138.56,130.35,129.70,129.60,129.50,128.96,128.72,128.52,127.75,126.47,125.92,125.75,119.39; HRMS(EI)Calcd.forC 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 AgOTf catalyst, 0.5 mmol (66 mg) of 3-phenyl acrolein, and 2 mL of toluene into the reaction vessel. At 110 o C was reacted in an oil bath for 10 hours, cooled to room temperature, the product was extracted with ethyl acetate, and concentrated under reduced pressure. The product was purified by column chromatography to obtain a white solid product with a yield of 90%.

Embodiment 3

[0031] Preparation of 4-phenyl-2-p-tolylquinoline: Add 0.5mmol (46.5mg) of aniline, AgOTf 0.005mmol (1.29mg), 3-phenyl-1-p-tolyl-?? Propylene ketone 0.5mmol (11.1mg), toluene 2mL. At 100 o C was reacted in an oil bath for 7 hours, cooled to room temperature, the product was extracted with ethyl acetate, and concentrated under reduced pressure. The product was purified by column chromatography to obtain a white solid product with a yield of 89%. 1 HNMR(500MHz, CDCl 3 )ppm:8.36(d, J =8.0Hz,1H),8.25(d, J =8.0Hz,2H),7.95-7.93(d, J =8.0Hz,1H),7.85(s,1H),7.81-7.74(m,1H),7.61-7.52(m,6H),7.38-7.36(d, J =8.0Hz,2H),2.46(s,3H); 13 CNMR(500MHz, 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; HRMS(EI)Calcd.forC 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 invention relates to quinoline derivatives, in particular to a method for efficiently synthesizing quinoline derivatives. It is a method for synthesizing quinoline derivatives with aniline and ketene or enal derivatives with silver trifluoromethanesulfonate catalytic substituent method. Background technique [0002] Quinoline compounds, as an important N-heterocyclic fine chemical raw material, have a wide range of applications in medicine, pesticides, spices, food, dyes, synthetic feed additives, and plant auxins. Quinoline compounds are widely present in nature, but separation and purification from nature not only has many operating steps, complicated separation devices, high energy consumption, high process cost, and serious environmental pollution. For example, quinoline can be obtained 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 obta...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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