Method for synthesizing 3-methylquinoline-8-sulfonyl chloride

A technology of methylquinoline and a synthesis method, applied in the chemical field, can solve the problems of imperfect post-processing, cumbersome operation, low yield and the like, and achieve the effects of high practical value, good economic benefit and low production cost

Inactive Publication Date: 2014-01-01
EAST CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] As an existing method patent (US6235778, CN200610046254) discloses a method for preparing 3-methylquinoline-8-sulfonyl chloride, but only limited to the preparation of 3-methylquinoline-8 from 3-methylquinoline -sulfonyl chloride this step reaction
Simultaneously, there are still some problems not solved in the synthetic method of this step, the product contains a large amount of hydrogen chloride to make the product yellow, and because the operation is complicated and the post-treatment is not perfect, the yield of the method is not high.

Method used

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  • Method for synthesizing 3-methylquinoline-8-sulfonyl chloride
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  • Method for synthesizing 3-methylquinoline-8-sulfonyl chloride

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preparation example Construction

[0040] The synthetic method of 3-methylquinoline-8-sulfonyl chloride of the present invention, take aniline as raw material and obtain N-phenylpropanamide through reacting with propionic acid, then form a ring to obtain 2-chloro-3-methylquinoline, After reduction with halogenated hydrocarbons, 3-methylquinoline is obtained, and then through chlorosulfonation to obtain the product 3-methylquinoline-8-sulfonyl chloride. The inventive method specifically comprises the following steps:

[0041] The first step is to prepare N-phenylpropanamide (as shown in the following formula (2)) with aniline (as shown in the following formula (1)) as a starting material

[0042]

[0043] React aniline, propionic acid and vitamin B1, heat to 120°C, react for 10 hours, stop heating, cool to room temperature, slowly pour the reaction system into ice water with stirring, stir for 15 minutes, filter the precipitated solid, wash with water twice, Then, beating and filtering with water, the solid ...

Embodiment 1

[0060] Synthesis of N-phenylpropanamide

[0061] Connect a thermometer to a 500mL three-necked flask, reflux the condenser, add aniline (100g, 1.07mol), propionic acid (90mL, 1.2mol), vitamin B1 (10g, 34mmol) at one time, heat at 120°C, and react for 10 hours. After the reaction is over, slowly pour the reaction system into 500 mL of ice water with stirring, stir for 15 min, filter the precipitated solid, wash twice with 2x100 mL of water, make a pulp and then filter, and dry the solid at 60 ° C. The light yellow solid N-phenylpropane Amide, 90% yield.

[0062] The nuclear magnetic spectrum of the N-phenylpropanamide prepared by the present embodiment is as follows figure 1 shown.

[0063] 1 HNMR (400MHz, CDCl 3 ) 7.5(d, 2H), 7.3(t, 2H), 7.1(s, 1H), 7.08~7.1(t, 1H), 2.36~2.42(m, 2H), 1.2(t, 3H).

[0064] Synthesis of 2-chloro-3-methylquinoline

[0065] Connect a thermometer, a reflux condenser, and a conduit to a 250mL three-necked flask. One end of the conduit is connec...

Embodiment 2

[0080] Synthesis of N-phenylpropanamide

[0081] Connect a thermometer to a 500mL three-necked flask, reflux the condenser, add aniline (100g, 1.07mol), propionic acid (110mL, 1.5mol), vitamin B1 (10g, 34mmol) at one time, heat at 100°C, and react for 10 hours. After the reaction, the reaction system was poured into 500mL of water, stirred for 15min, the precipitated solid was filtered, washed twice with 2x100mL of water, and the solid was dried at 60°C. The yellow solid N-phenylpropanamide yielded 85%.

[0082] Synthesis of 2-chloro-3-methylquinoline

[0083] Connect a thermometer, a reflux condenser, and a conduit to a 250mL three-necked flask. One end of the conduit is connected to a water tank, and N, N-dimethylformamide (12.20mL, 0.15mol) is added. Add oxalyl chloride (57mL, 0.6mol) dropwise, solidification will occur during the dropwise addition, continue to drop and the solidification will disappear, then add N-phenylpropanamide (15g, 0.1mol), after the addition, store...

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Abstract

The invention discloses a method for synthesizing 3-methylquinoline-8-sulfonyl chloride. The method comprises the steps: with aniline as a starting material, carrying out a reaction with propionic acid to obtain N-phenylpropionamide, then generating a ring to obtain 2-chloro-3-methylquinoline, next carrying out halogenated hydrocarbon reduction to obtain 3-methylquinoline, and finally carrying out chlorosulfonation to obtain the product 3-methylquinoline-8-sulfonyl chloride. The method is low in cost, simple in operation, good in economic benefits, high in yield, and suitable for industrialized production. With the method of the invention, 3-methylquinoline-8-sulfonyl chloride can be obtained with high yield rate.

Description

technical field [0001] The invention relates to a synthesis method of 3-methylquinoline-8-sulfonyl chloride, which belongs to the technical field of chemical industry. Background technique [0002] In existing patent (US4201863, EP8746, US4258192, CN200610046254) introduced a kind of chemical synthesis process of novel drug-Argatroban (Argatrban) for the treatment of acute ischemic stroke, and 3-methylquin Phenyl-8-sulfonyl chloride was used as an intermediate in this process. 3-Methylquinoline-8-sulfonyl chloride has a chemical structure shown in the following formula (5). [0003] [0004] As an existing method patent (US6235778, CN200610046254) discloses a method for preparing 3-methylquinoline-8-sulfonyl chloride, but only limited to the preparation of 3-methylquinoline-8 from 3-methylquinoline -sulfonyl chloride this step reaction. Simultaneously, there are still some problems not solved in the synthetic method of this step. The product contains a large amount of ...

Claims

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Application Information

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IPC IPC(8): C07D215/36
CPCC07D215/36
Inventor 胡文浩吴为贲姜宗光周静杨琍苹
Owner EAST CHINA NORMAL UNIVERSITY
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