Synthetic method for drug intermediate 1-methyl-2-quinolinone

A synthesis method and intermediate technology, applied in the field of organic synthesis, can solve the problems of high health hazards for synthesis operators, increased risk coefficient in the synthesis process, corrosion and environmental hazards, etc., to avoid health hazards, avoid burning decomposition, and risk factors Reduced effect

Inactive Publication Date: 2018-07-03
CHENGDU KA DI FU TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] 1-Methyl-2-quinolinone is mainly used in the synthesis of pharmaceutical intermediates. Most of the existing synthetic methods use quinoline, dimethyl sulfate, sodium hydroxide solution, potassium ferricyanide and other raw materials as reactants. The dimethyl sulfate used in this synthetic method is a potential carcinogen and a mutagen that can cause chromosomal aberrations. It is volatile, toxic, corrosive and environmentally harmful, and can be absorbed through the skin, mucous membranes and gastrointestinal tract. Hazardous to health; sodium hydroxide solution is extremely corrosive, and its solution or dust splashed on the skin, especially the mucous membrane, can produce soft scabs, and can penetrate into deep tissues, leaving scars after burns, splashing human eyes It will not only damage the cornea, but also damage the deep tissue of the eye, so it will increase the safety risk as a synthetic raw material; the burning decomposition of potassium ferricyanide or the production of highly toxic cyanide when it encounters acid will also lead to an increase in the risk factor of the synthesis process; therefore, the above-mentioned Factors will cause this synthetic method to have many shortcomings, it is necessary to propose a new synthetic method

Method used

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  • Synthetic method for drug intermediate 1-methyl-2-quinolinone
  • Synthetic method for drug intermediate 1-methyl-2-quinolinone
  • Synthetic method for drug intermediate 1-methyl-2-quinolinone

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Experimental program
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Effect test

Embodiment 1

[0017] The synthetic method of medicine intermediate 1-methyl-2-quinolinone, comprises the steps:

[0018] A: Add 3mol 2-methylquinoline in reaction vessel, 800ml mass fraction is 30% 2-chlorophenol solution, control solution temperature to 20 ℃, add 6mol aqueous solution, 1.2L mass fraction is 10% butane solution , control the stirring speed to 210rpm, and react for 90min;

[0019] B: Then add 600ml of potassium chloride solution with a mass fraction of 20%, 6mol iridium dioxide powder, raise the temperature to 30°C, continue the reaction for 1h, lower the temperature to 5°C, separate the layers, and use a mass fraction of 5% for the oil layer The sodium nitrate solution was washed for 30 minutes, the diglyme solution with a mass fraction of 70% was washed for 20 minutes, recrystallized in a sulfolane solution with a mass fraction of 80%, and the dehydrating agent activated alumina was dehydrated to obtain the finished product 1-methyl- 2-quinolinone 464.598g, yield 97.4%. ...

Embodiment 2

[0021] The synthetic method of medicine intermediate 1-methyl-2-quinolinone, comprises the steps:

[0022] A: Add 3mol 2-methylquinoline in reaction vessel, 800ml mass fraction is 33.5% 2-chlorophenol solution, control solution temperature to 23 ℃, add 7.5mol aqueous solution, 1.2L mass fraction is 13% butane solution, control the stirring speed to 220rpm, and react for 105min;

[0023] B: Then add 600ml of potassium chloride solution with a mass fraction of 22.5%, 7mol iridium dioxide powder, raise the temperature to 32.5°C, continue the reaction for 1.5h, lower the temperature to 7°C, separate the solutions, and use a mass fraction of 8 for the oil layer % sodium nitrate solution for 40 min, and a mass fraction of 74% diglyme solution for 30 min, then recrystallized in a sulfolane solution with a mass fraction of 83%, dehydrating with a dehydrating agent activated alumina to obtain the finished product 1-methyl - 465.552 g of 2-quinolinone, yield 97.6%.

Embodiment 3

[0025] The synthetic method of medicine intermediate 1-methyl-2-quinolinone, comprises the steps:

[0026] A: Add 3mol 2-methylquinoline in reaction vessel, 800ml mass fraction is 37% 2-chlorophenol solution, control solution temperature to 26 ℃, add 9mol aqueous solution, 1.2L mass fraction is 16% butane solution , control the stirring speed to 230rpm, and react for 120min;

[0027] B: Then add 600ml of potassium chloride solution with a mass fraction of 25%, 8mol of iridium dioxide powder, raise the temperature to 35°C, continue the reaction for 2h, lower the temperature to 9°C, separate the solutions, and use a mass fraction of 11% for the oil layer The sodium nitrate solution was washed for 50 minutes, and the diglyme solution with a mass fraction of 78% was washed for 40 minutes, recrystallized in a sulfolane solution with a mass fraction of 86%, and dehydrated by a dehydrating agent activated alumina to obtain the finished product 1-methyl- 2-quinolinone 467.937g, yield...

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Abstract

The invention discloses a synthetic method for the drug intermediate 1-methyl-2-quinolinone. The synthetic method is characterized by comprising the following steps: adding 2-methylquinoline and 2-chlorophenol solution into a reaction vessel, controlling a solutioni temperature, adding an aqueous solution and a butane solution, controlling a stirring speed, and then carrying out a reaction; and then adding a potassium chloride solution and iridic oxide powder, raising the temperature, continuing the reaction, lowering the temperature, subjecting the obtained solution to layering, washing a separated oil layer with a sodium nitrate solution, then washing the separated oil layer with a diethylene glycol dimethyl ether solution, carrying out recrystallization in a sulfolane solution, and thencarrying out dehydration with a dehydrating agent to obtain the finished 1-methyl-2-quinolinone.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, belonging to the field of organic synthesis, in particular to a synthesis method of a pharmaceutical intermediate 1-methyl-2-quinolinone. Background technique [0002] 1-Methyl-2-quinolinone is mainly used in the synthesis of pharmaceutical intermediates. Most of the existing synthetic methods use quinoline, dimethyl sulfate, sodium hydroxide solution, potassium ferricyanide and other raw materials as reactants. The dimethyl sulfate used in this synthetic method is a potential carcinogen and a mutagen that can cause chromosomal aberrations. It is volatile, toxic, corrosive and environmentally harmful, and can be absorbed through the skin, mucous membranes and gastrointestinal tract. Hazardous to health; sodium hydroxide solution is extremely corrosive, and its solution or dust splashed on the skin, especially the mucous membrane, can produce soft scabs, and can penetrate in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227
CPCC07D215/227
Inventor 廖如佴
Owner CHENGDU KA DI FU TECH
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