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Preparation method of environment-friendly quinoline compound

A compound, quinoline technology, which is applied in pharmaceutical and chemical intermediates and related chemical fields, can solve problems such as limitations, and achieve the effects of simple operation, environmental friendliness, and high yield

Active Publication Date: 2018-02-27
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2015, a method for preparing quinoline from N-benzylaniline was reported using radical cation salt as a catalyst, but the synthesis of the catalyst limited the development of this method [Liu J., Liu F., Zhu Y., Ma X. , Jia X., Org. Lett., 2015, 17, 1409]

Method used

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  • Preparation method of environment-friendly quinoline compound
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  • Preparation method of environment-friendly quinoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the synthesis of 2,4-diphenylquinoline

[0037] In a 25mL reactor, add N-benzylaniline (0.037g, 0.2mmol), phenylacetylene (0.102g, 1.0mmol), add trifluoroacetic acid (0.003g, 0.03mmol) under stirring, 80 ℃, oxygen bulb conditions Under stirring for 24h. Column chromatography separation (silica gel, 200-300 mesh; developer, petroleum ether / dichloromethane=4 / 1) gave 0.047 g of 2,4-diphenylquinoline with a yield of 83%.

[0038] 2,4-Diphenylquinoline

[0039] yellow oily liquid; 1 H NMR (400MHz, CDCl 3 ):δ8.23(d,J=8.4Hz,1H),8.19(d,J=8.4Hz,2H),7.91(d,J=8.3Hz,1H),7.82(s,1H),7.75–7.71 (m,1H),7.57–7.46(m,9H); 13 CNMR (125MHz, CDCl 3 ): δ156.8, 149.1, 148.8, 139.6, 138.4, 130.1, 129.5, 129.5, 129.3, 128.8, 128.6, 128.4, 127.5, 126.3, 125.7, 125.6, 119.3.

Embodiment 2

[0040] Embodiment 2: Synthesis of 2-(5-bromothienyl-2-)-6-methyl-4-phenylquinoline

[0041] Operation is the same as in Example 1, by reacting N-[(5-bromothienyl-2-)methyl]-4-methylaniline with phenylacetylene to obtain 2-(5-bromothienyl-2-)-6-methanol Base-4-phenylquinoline 0.059g, yield 78%.

[0042] 2-(5-Bromothienyl-2-)-6-methyl-4-phenylquinoline

[0043] Brown solid; melting point 181.1–182.0°C; 1 H NMR (400MHz, CDCl 3 ):δ8.01(d, J=8.6Hz, 1H), 7.56–7.50(m, 8H), 7.42(d, J=4.0Hz, 1H), 7.06(d, J=4.0Hz, 1H), 2.43 (s, 3H); 13C NMR (100MHz, CDCl 3 ):δ149.8,148.9,146.6,138.0,136.5,132.2,131.0, 129.4,128.9,128.6,128.5,125.8,125.7,124.5,117.1,116.0,21.8; HRMS(ESI,m / z) calcd for C 20 h 15 NBrS + :380.0103[M+H] + ;found:380.0109;IR(neat)3046,2959,2825,1608,1563,1442,1021,850,790,732,574cm -1 .

Embodiment 3

[0044] Embodiment 3: Synthesis of 2-(3,4-dichlorophenyl)-6-methyl-4-phenylquinoline

[0045] The operation is the same as in Example 1, and 2-(3,4-dichlorophenyl)-6-methyl-4- Phenylquinoline 0.067g, yield 92%.

[0046] 2-(3,4-Dichlorophenyl)-6-methyl-4-phenylquinoline

[0047] White solid; melting point 143.0–143.6°C; 1 H NMR (400MHz, CDCl 3 ):δ8.11(d,J=8.5Hz, 1H),7.71–7.68(m,2H),7.62(s,1H),7.58–7.48(m,7H),7.37(dd,J=8.5,2.1 Hz, 1H), 2.47(s, 3H); 13 C NMR (125MHz, CDCl 3 ): δ154.8, 147.5, 147.2, 138.1, 138.1, 137.0, 135.0, 133.1, 132.6, 131.8, 129.8, 129.7, 129.5, 128.5, 128.3, 127.4, 125.6, 124.4, 122.7, 21.8.

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Abstract

The invention belongs to the technical field of medical and chemical intermediates and relevant chemistry, and provides a preparation method of an environment-friendly quinoline compound. The preparation method is characterized in that a N-substituted polyaniline derivative serving as a raw material reacts with a phenylacetylene or styrene derivative in the presence of a Bronsted acid catalyst andan oxidizing agent and in the absence of a solvent at the temperature of 80 to 160 DEG C for 24 hours to obtain the quinoline compound. The preparation method has the beneficial effects of easiness and convenience in operation, mild conditions, environmental friendliness, probability of realizing industrial production and higher yield of the quinoline compound. The quinoline compound synthesizedby the preparation method can be further functionalized to obtain various compounds, and is applied to the development and researches of natural products, function materials and fine chemicals.

Description

technical field [0001] The invention belongs to the field of pharmaceutical and chemical intermediates and related chemical technologies, and relates to a preparation method of a green quinoline compound. Background technique [0002] Quinoline compounds are an extremely important structural unit in organic chemistry, and they have very important application values ​​in the fields of medicine, pesticides, dyes, functional materials and spices. Since quinoline was isolated from coal tar by Runge in 1834, how to use chemical methods to synthesize quinoline derivatives has been a hot research topic for organic synthetic chemists. [0003] Classical chemical methods for the organic synthesis of quinoline derivatives include Skraup–Doebner–von Miller synthesis, Combes–Conrad–Limpach synthesis, synthetic method and Pfitzinger synthetic method [Fallah-Mehrjardi M., Mini-Rev. Org. Chem., 2017, 14, 187], these synthetic methods have a great disadvantage that they are usually carrie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/06C07D409/04C07D215/12C07D215/48C07D215/14
CPCC07D215/06C07D215/12C07D215/14C07D215/48C07D409/04B01J31/0225B01J31/0227B01J31/04B01J2231/30B01J2231/324
Inventor 张胜包明艾哈迈德·瓦卡于晓强冯秀娟
Owner DALIAN UNIV OF TECH
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