Synthetic method for anti-amebic-dysentery drug phanquone

A technology of phenanthrenediridone and a synthesis method, which is applied in the field of organic synthesis, can solve the problems of complex process, high corrosion resistance requirements, increased production cost, etc., and achieves the improvement of reaction yield, reduction of reaction intermediate links, and improvement of reaction yield. Effect

Inactive Publication Date: 2018-07-03
CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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  • Abstract
  • Description
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Problems solved by technology

This synthesis method needs to use nitric acid and concentrated sulfuric acid as reactants. Due to the strong oxidizing and corrosive properties of nitric acid and concentrated sulfuric acid, the requirements for corrosion resistance of equipment are relatively high, the production cost also increases thereupon, and the process is relatively complicated. Therefore, it is necessary to propose A new synthetic method

Method used

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  • Synthetic method for anti-amebic-dysentery drug phanquone

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Effect test

Embodiment 1

[0016] The synthetic method of anti-amoebic dysentery drug phenanthrene diridone comprises the following steps:

[0017] A: Add 3mol 5-hydroxy-6-methoxy-4,7-phenanthrene, 1.6L potassium chloride solution with a mass fraction of 10% in the reaction vessel, raise the temperature of the solution to 30°C, and control the stirring Speed ​​230rpm, reaction 2h;

[0018] B: Add 900ml of sodium sulfate solution with a mass fraction of 20%, increase the temperature of the solution to 50°C, then add a 6mol diethyl sebacate solution with a mass fraction of 35%, and add 3mol of diethyl sebacate in 3 times within 50min Cobalt powder, reacted for 90min, lowered the temperature to 10°C, adjusted the pH to 5.5, washed 5 times with 40% benzyl chloride solution, 6 times with 60% 2,3-dimethylbutane solution, Recrystallize in 2,4-dichlorotoluene solution with a mass fraction of 80%, and dehydrate with anhydrous magnesium sulfate dehydrating agent to obtain 548.1 g of finished phenanthrene diridon...

Embodiment 2

[0020] The synthetic method of anti-amoebic dysentery drug phenanthrene diridone comprises the following steps:

[0021] A: Add 3mol 5-hydroxy-6-methoxy-4,7-phenanthrene in the reaction vessel, 1.6L mass fraction is 13% potassium chloride solution, raise the solution temperature to 35°C, and control the stirring speed 250rpm, reaction 2.5h;

[0022] B: Add 900ml mass fraction of 23% sodium sulfate solution, increase the temperature of the solution to 55°C, then add 7mol diethyl sebacate solution with a mass fraction of 38%, add 3.5mol diethyl sebacate in 4 times within 60min Cobalt powder, react for 110min, lower the temperature to 13°C, adjust the pH to 5.7, wash 5 times with 43% benzyl chloride solution, 6 times with 62% 2,3-dimethylbutane solution , recrystallized in a 2,4-dichlorotoluene solution with a mass fraction of 83%, and dehydrated with an activated alumina dehydrating agent to obtain 573.3 g of the finished phenanthrene diridone, with a yield of 91%.

Embodiment 3

[0024] The synthetic method of anti-amoebic dysentery drug phenanthrene diridone comprises the following steps:

[0025] A: Add 3mol of 5-hydroxy-6-methoxy-4,7-phenanthrene in the reaction vessel, 1.6L mass fraction is 17% potassium chloride solution, raise the temperature of the solution to 40°C, and control the stirring Speed ​​260rpm, reaction 3h;

[0026] B: Add 900ml mass fraction of 26% sodium sulfate solution, increase the temperature of the solution to 60°C, then add 8mol diethyl sebacate solution with a mass fraction of 41%, add 4mol diethyl sebacate in 5 times within 70min powder, reacted for 120min, lowered the temperature to 17°C, adjusted the pH to 6, washed 7 times with 46% benzyl chloride solution, 8 times with 65% 2,3-dimethylbutane solution, Recrystallize in 2,4-dichlorotoluene solution with a mass fraction of 87%, and dehydrate with anhydrous potassium carbonate dehydrating agent to obtain 592.2 g of finished phenanthrene diridone, with a yield of 94%.

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Abstract

The invention discloses a synthetic method for the anti-amebic-dysentery drug phanquone. The synthetic method comprises the following steps: adding 5-hydroxy-6-methoxy-4,7-diazaphenanthrene and a potassium chloride solution into a reaction vessel, raising a solution temperature, controlling a stirring speed, and carrying out a reaction; and adding a sodium sulfate solution, raising the solution temperature, then adding a diethyl sebacate solution, adding cobaltocene powder in batches within a certain period of time, carrying out a reaction, lowering the temperature, adjusting a pH value, thencarrying out washing with a benzyl chloride solution a plurality of times, then carrying out washing with a 2,3-dimethylbutane solution a plurality of times, carrying out recrystallization in a 2,4-dichlorotoluene solution, and then carrying out dehydration with a dehydrating agent so as to obtain the finished phanquone.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, which belongs to the field of organic synthesis, in particular to a synthesis method of an anti-amoebic dysentery drug phenanthrene diridone. Background technique [0002] Phenanthrene diridone drugs are mainly used for anti-amoebic dysentery and bacillary dysentery drugs. Most of the existing synthetic methods use o-acetamidoanisole through nitration, reduction, and hydrolysis to generate 2,5-diaminoanisole sulfate. Then it reacts with glycerin and concentrated sulfuric acid under the presence of iodine and potassium iodide, and undergoes ring closure to obtain 6-methoxy-4,7-phenanthroline, which is further oxidized to obtain the finished product. This synthesis method needs to use nitric acid and concentrated sulfuric acid as reactants. Due to the strong oxidizing and corrosive properties of nitric acid and concentrated sulfuric acid, the requirements for corrosion resist...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 关艮安
Owner CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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