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A kind of method for preparing 7-hydroxyl-2-quinolone

A quinolone, hydroxyl technology, applied in the field of pharmaceutical synthesis technology, can solve the problems of long synthesis route, low product cost, many side reactions, etc., and achieve the effects of short reaction route, reduced product cost, and easy availability of raw materials

Active Publication Date: 2019-07-02
CANGZHOU SENARY CHEM SCI TEC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved in the present invention is to provide a method for preparing 7-hydroxy-2-quinolone for the deficiencies of the above-mentioned prior art, which solves the problems of long synthetic route, complex process and many side reactions, and has a reaction route Short, simple process, easy to obtain raw materials, high product yield, low product cost, suitable for industrial application

Method used

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  • A kind of method for preparing 7-hydroxyl-2-quinolone
  • A kind of method for preparing 7-hydroxyl-2-quinolone
  • A kind of method for preparing 7-hydroxyl-2-quinolone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 240mL of water and 36.8g of sodium hydroxide to a 500mL three-necked flask, stir and dissolve completely, then add 30g of 7-hydroxy-3,4-dihydro-2(1H)-quinolinone, stir evenly; heat up to 50-60°C, Then add 96g of active manganese dioxide in batches (add 8-10g every 5 minutes), keep the reaction temperature at 50-60°C for 7-8h; 20:1), after the reaction, the system was cooled to 30-40°C, filtered, and the filter cake was washed with 50mL 8% sodium hydroxide solution; the filtrate was combined and transferred to a three-necked flask, 3g of activated carbon was added, and the temperature was raised to 60-70°C. Stir for 1-2h, carry out decolorization treatment; filter the solution after decolorization treatment, adjust the pH of the filtrate to 2-3 with concentrated hydrochloric acid; then filter to obtain the product filter cake, use 50mL water to rinse the product filter cake, and obtain The filter cake was dried at 40-50° C. to obtain 18.0 g of 7-hydroxy-2-quinolone w...

Embodiment 2

[0030] Add 240mL of water and 18.4g of sodium hydroxide to a 500mL three-necked flask, stir and dissolve completely, then add 30g of 7-hydroxy-3,4-dihydro-2(1H)-quinolinone, stir evenly; heat up to 50-60°C, Add 48g of active manganese dioxide in batches (8-10g every 5 minutes), keep the reaction temperature at 50-60°C for 12-13h; TLC to identify the reaction end point (developing agent: dichloromethane-methanol, volume ratio 20 : 1), after the reaction is completed, the system is cooled to 30-40°C, filtered, and the filter cake is washed with 50mL of 8% sodium hydroxide solution; 1-2h, carry out decolorization treatment; filter the solution after decolorization treatment, adjust the pH of the filtrate to 2-3 by concentrated hydrochloric acid; then filter to obtain the product filter cake, use 50mL water to rinse the product filter cake, and obtain the filter cake Dry the cake at 40-50° C. to obtain 18.3 g of 7-hydroxy-2-quinolone with a yield of 61.0%.

[0031] 1 HNMR (DMSO-...

Embodiment 3

[0033] Add 240mL of water and 25.7g of sodium hydroxide to a 500mL three-necked flask, stir and dissolve completely, then add 30g of 7-hydroxy-3,4-dihydro-2(1H)-quinolinone, stir evenly; heat up to 60-70°C, Add 72g of active manganese dioxide in batches (8-10g every 5 minutes), keep the reaction temperature at 60-70°C for 7-8h; TLC to identify the reaction end point (developing agent: dichloromethane-methanol, volume ratio 20 : 1), after the reaction is completed, the system is cooled to 30-40°C, filtered, and the filter cake is washed with 50mL of 8% sodium hydroxide solution; 1-2h, carry out decolorization treatment; filter the solution after decolorization treatment, adjust the pH of the filtrate to 2-3 by concentrated hydrochloric acid; then filter to obtain the product filter cake, use 50mL water to rinse the product filter cake, and obtain the filter cake Dry the cake at 40-50° C. to obtain 18.6 g of 7-hydroxy-2-quinolone with a yield of 63%.

[0034] 1 HNMR (DMSO-d 6...

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Abstract

The invention discloses a method for preparing 7-hydroxy-2-quinolone, which relates to the technical field of pharmaceutical synthesis. In the method, raw materials of 7-hydroxy-3,4-dihydro-2(1H)-quinolone are added to inorganic In the alkaline solution, heat up to the reaction temperature, the reaction temperature is 40-80°C, oxidize with active manganese dioxide, and separate the 7-hydroxy-2 quinolone from the resulting liquid after the end of the reaction to obtain the product. The invention has the characteristics of short reaction route, simple process, easy-to-obtain raw materials, product yield over 60%, product cost reduction of 20-30%, and is suitable for industrial application.

Description

technical field [0001] The invention relates to the technical field of medicine synthesis technology, in particular to a method for preparing 7-hydroxy-2-quinolone. Background technique [0002] Brexpiprazole (brexpiprazole) is the first dopamine, partial 5-HT drug jointly developed by Otsuka Pharmaceutical and Lundbeck Pharmaceutical Company 1A Agonists and 5-HT 2A Receptor antagonist compound, launched in the United States on July 10, 2015. For the treatment of schizophrenia in adults, and in combination with antidepressants for the treatment of major depression in adults. 7-Hydroxy-2-quinolone is an important intermediate in the preparation of ebiprazole. [0003] Regarding the method for preparing 7-hydroxyl-2-quinolones, according to published literature reports, there are: 1. with acetone and ethyl acrylate as raw materials, ring closure generates 3-(2,4-dioxo-cyclohexyl)-propionic acid Ethyl ester, after protection, amine transesterification, and ring closure to o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/22
CPCC07D215/22
Inventor 于淑玲刘劲松张少平王平王伟佟建强
Owner CANGZHOU SENARY CHEM SCI TEC