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A kind of synthetic method of 3,7-dichloro-8-quinoline formyl chloride

A synthetic method, quinolineformyl technology, applied in the field of artificial antigen synthesis, can solve the problems of increasing the difficulty of "three wastes" and "three wastes" treatment, unfavorable safety and environmental protection, and high energy consumption of various solvents, achieving low cost, The effect of good product quality and shortened reaction time

Active Publication Date: 2022-03-29
赵东源 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The synthesis of artificial antigen intermediate 3,7-dichloro-8-quinoline formyl chloride is mostly synthesized by solvent method. Synthesis method 1: use oxalyl chloride and 3,7-dichloro-8-quinoline acid as raw materials, and use Dichloromethane is used as a solvent and DMF is used as a co-solvent for synthesis. First, Class A dangerous goods are used; second, the cost of oxalyl chloride is high; third, the amount of waste water is large, which is not conducive to safety and environmental protection; fourth, the separation and recovery of multiple solvents requires high energy consumption. , equipment investment is large, and the purity is low
Synthesis method 2: Thionyl chloride and 3,7-dichloro-8-quinolinic acid are used as raw materials and DMF is used as a solvent to synthesize. In addition to the disadvantages of the above-mentioned synthesis method 1, SO is also produced during the reaction process. 2 and HC1 gas, increasing the difficulty of "three wastes" and "three wastes" treatment

Method used

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  • A kind of synthetic method of 3,7-dichloro-8-quinoline formyl chloride
  • A kind of synthetic method of 3,7-dichloro-8-quinoline formyl chloride

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Example 1 Synthesis of 3,7-dichloro-8-quinoline formyl chloride

[0027] (1) In a 250ml four-neck flask equipped with a magnetic stirrer, a thermometer and a lead tube condenser, add 24.2g3,7-dichloro-8-quinolinic acid and 45.2g monochloroacetyl chloride, and in the process of stirring 0.12 g of catalyst anhydrous aluminum trichloride was added, the condenser was turned on to lower the temperature, and the temperature was slowly raised to 100°C-115°C, and the reaction was refluxed at this temperature for 1.5h.

[0028] (2) Sampling control, when the content of 3,7-dichloro-8-quinolinic acid is ≤0.5%, the reaction end point is reached, the temperature is lowered to 50°C, filtered, and the filtrate is collected for later use.

[0029] (3) the filter cake is washed twice with chloroacetyl chloride, each washing with 10g of chloroacetyl chloride, the combined washing liquid and the filtrate collected in step (2), then underpressure distillation, and then after 95 ℃ of under...

Embodiment 2

[0030] Example 2 Synthesis of 3,7-dichloro-8-quinoline formyl chloride

[0031] With step (1), middle catalyst aluminum trichloride is replaced by anhydrous iron trichloride, other is identical with embodiment 1, obtains pale yellow 3,7-dichloro-8-quinoline formyl chloride 25.3g, yield It is 94.3% and the purity is 97.1%.

Embodiment 3

[0032] Example 3 Synthesis of 3,7-dichloro-8-quinoline formyl chloride

[0033] In step (1), the amount of monochloroacetyl chloride was modified to 33.9g, and the others were the same as in Example 1 to obtain 25.7g of pale yellow 3,7-dichloro-8-quinoline carboxylic acid chloride, with a yield of 96.48% , with a purity of 97.8%.

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Abstract

The invention relates to a method for synthesizing 3,7-dichloro-8-quinolineformyl chloride. Under the condition that no solvent exists, 3,7-dichloro-8-quinolinic acid, monochloroacetyl chloride and a catalyst The acylation reaction is carried out at 95°C-120°C, after filtration, washing and distillation under reduced pressure, the compound represented by formula I is obtained, and the specific synthetic route is as follows. In the process of the reaction, a catalyst is used, no solvent needs to be added, the source of raw materials is easily available, the cost is low, the process steps are few, the reaction conditions are mild, no special equipment is required, the product quality is good, the purity is high, and the yield is higher than 95%, No waste water and waste gas, relatively safe and environmentally friendly.

Description

technical field [0001] The invention belongs to the technical field of artificial antigen synthesis, and in particular relates to a synthesis method of 3,7-dichloro-8-quinoline carboxylic acid chloride. Background technique [0002] The synthesis of artificial antigen intermediate 3,7-dichloro-8-quinoline formyl chloride is mostly synthesized by solvent method. Synthesis method 1: use oxalyl chloride and 3,7-dichloro-8-quinoline acid as raw materials, and use Dichloromethane is used as a solvent and DMF is used as a co-solvent for synthesis. First, Class A dangerous goods are used; second, the cost of oxalyl chloride is high; third, the amount of waste water is large, which is not conducive to safety and environmental protection; fourth, the separation and recovery of multiple solvents consumes a lot of energy. , equipment investment is large, and the purity is low. Synthesis method 2: Thionyl chloride and 3,7-dichloro-8-quinolinic acid are used as raw materials and DMF is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/48
CPCC07D215/48
Inventor 赵东源贺川徐大鹏
Owner 赵东源
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