Synthesis method of 7-chloroquinaldine

A synthetic method, the technology of chloroquine, which is applied in the field of synthesis of 7-chloroquinaldine, achieves the effect of strong market competitiveness, good stability and low price

Active Publication Date: 2018-11-16
马海红
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no better synthesis process that can simplify the operation steps and achieve high reaction yield, easy purification, good economy and industrial production.

Method used

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  • Synthesis method of 7-chloroquinaldine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] A kind of synthetic method of 7-chloroquinaldine is characterized in that the method comprises the following steps:

[0017] Step 1. Install a thermometer, a dropping funnel and a reflux condenser on a 500 ml three-necked bottle. Add o-nitrotoluene 34.0g, 3.4gSiO2 to the bottle 2 -HEPIMBr catalyst and mass fraction 30% hydrochloric acid 240ml;

[0018] Step 2. After mixing evenly, slowly add m-chloroaniline 104.0g and heat up to 100°C, slowly drop 68.0g crotonaldehyde into the system, after 5h, after reflux at reflux temperature for 4h, steam distillation to remove o-nitrotoluene and dilute hydrochloric acid;

[0019] Step 3, the residual liquid in the bottle is neutralized with ammonia water with a mass fraction of 28% to pH = 7, and the activated carbon removes impurities to obtain an oily liquid;

[0020] Step 4. Distill the above-mentioned oily liquid under reduced pressure to collect oily fractions at 175-185° C. / 5.5 kPa, which become solid after cooling, and re...

Embodiment 2

[0027] Step 2. After mixing evenly, slowly add m-chloroaniline 94.0g and raise the temperature to 100°C, slowly add 68.0g crotonaldehyde into the system, after 5h, after reflux at reflux temperature for 4h, steam distillation to remove o-nitrotoluene And dilute hydrochloric acid; All the other steps are with embodiment 1.

Embodiment 3

[0029] Step 2. After mixing evenly, slowly add 84.0g of m-chloroaniline dropwise and raise the temperature to 100°C, slowly add 68.0g of crotonaldehyde into the system dropwise, after 5h, reflux at reflux temperature for 4h, steam distillation to remove o-nitrotoluene And dilute hydrochloric acid; All the other steps are with embodiment 1.

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Abstract

The invention discloses a synthesis method of 7-chloroquinaldine. 2-nitrotoluene, SiO2-HEPIMBr, m-chloroaniline, crotonaldehyde, TEOS, 2-bromoethanol, imidazole and 3-chloropropyltriethoxysilane are taken as main raw materials. According to the synthesis process, m-chloroaniline and crotonaldehyde are subjected to Skraup reaction under action of an immobilized ion catalyst SiO2-HEPIMBr, and 7-chloroquinaldine is obtained. SiO2 immobilized hydroxyl ionic liquid HEPIMBr is prepared with a grafting method, in the reaction, few by-products are produced and no 5-isomer is produced, so that the separation and purification process is reduced, purity of a product is improved, yield of the product is increased, and higher market competitiveness is achieved.

Description

technical field [0001] The invention relates to a synthesis method of 7-chloroquinaldine, which belongs to the field of chemical synthesis. Background technique [0002] 7-Chloroquinaldine CAS: 4965-33-7, is a kind of off-white crystal, which is stable at normal temperature and pressure, and can be applied to montelukast, an important anti-asthma drug newly developed in recent years. Triene D4 receptor antagonist) synthesis. In view of its important medical use, people have carried out a lot of in-depth research on the synthesis technology of 7-chloroquinaldine. At present, this product is usually prepared by using 3-chloroaniline and 2-butenal as main raw materials and nitrobenzene derivatives as oxidants by performing classic Skraup reaction or Doebne-Miller reaction. However, due to the simultaneous generation of isomer 5-chloroquinaldine in the reaction, the yield is low, and the subsequent separation and purification process is cumbersome, resulting in high cost. The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/18B01J31/02
CPCB01J31/0295B01J2231/324C07D215/18
Inventor 不公告发明人
Owner 马海红
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