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8-hydroxyquinoline and synthetic method thereof

A technology of hydroxyquinoline and a synthetic method, which is applied in the field of biomedicine, can solve the problems of many by-products, limited yield, expensive and difficult-to-obtain raw materials of 8-hydroxyquinoline, achieve less by-products, improve purity, and be easy to implement Effect

Inactive Publication Date: 2016-07-13
叶芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials used in the preparation of 8-hydroxyquinoline by this method are still expensive and difficult to obtain, and there are still many by-products, and the yield is limited

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1. Dissolve 0.06g of nickel trioxide in 200mL of concentrated sulfuric acid, stir at room temperature, and add 30mL of glacial acetic acid dropwise therein, and continue stirring for 1 hour after the dropwise addition to obtain the catalyst;

[0021] 2. Add 1mol of o-aminophenol, 1.5mol of anhydrous glycerin, and 1mol of o-nitrophenol into the reaction kettle, stir vigorously, drop in 100ml of the catalyst obtained in the above steps, keep stirring at 70°C for 5 hours, and wait for the reaction to complete , adjust the pH to 7 with 40% sodium hydroxide solution, distill to obtain the crude product of 8-hydroxyquinoline, and obtain the pure product of 8-hydroxyquinoline after recrystallization from ethanol.

[0022] The purity of the obtained 8-hydroxyquinoline was 95%, and the yield was 85.2%.

Embodiment 2

[0024] 1. Dissolve 0.06g of nickel trioxide in 200mL of concentrated sulfuric acid, stir at room temperature, and add 25mL of glacial acetic acid dropwise therein, and continue stirring for 1 hour after the dropwise addition to obtain the catalyst;

[0025] 2. Add 1mol of o-aminophenol, 1mol of anhydrous glycerin, and 1.5mol of o-nitrophenol into the reaction kettle, stir vigorously, drop in 150ml of the catalyst obtained in the above steps, keep stirring at 80°C for 5h, and wait until the reaction is completed , adjust the pH to 7.5 with ammonia solution, distill to obtain crude 8-hydroxyquinoline, and obtain pure 8-hydroxyquinoline after recrystallization from ethanol.

[0026] The purity of the obtained 8-hydroxyquinoline was 95.5%, and the yield was 86.8%.

Embodiment 3

[0028] 1. Dissolve 0.08g of nickel trioxide in 200mL of concentrated sulfuric acid, stir at room temperature, and add 430mL of glacial acetic acid dropwise therein, and continue stirring for 1 hour after the dropwise addition to obtain the catalyst;

[0029] 2. Add 1mol of o-aminophenol, 1.5mol of anhydrous glycerin, and 2mol of o-nitrophenol into the reaction kettle, stir vigorously, drop in 200ml of the catalyst obtained in the above steps, keep stirring at 90°C for 5 hours, and wait for the reaction to complete , adjust the pH to 8 with 40% sodium hydroxide solution, distill to obtain the crude product of 8-hydroxyquinoline, and obtain the pure product of 8-hydroxyquinoline after recrystallization from ethanol.

[0030] The purity of the obtained 8-hydroxyquinoline was 97.1%, and the yield was 92.7%.

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Abstract

The invention discloses 8-hydroxyquinoline and a synthetic method thereof.Ortho-aminophenol, anhydrous glycerol and o-nitrophenol are used as raw materials in the synthetic method.The synthetic method includes the steps of (1), dissolving nickel sesquioxide in concentrated sulfuric acid, stirring at room temperature, dropwise adding glacial acetic acid into a mixture, and stirring continuously for 1 hour after dropwise adding is completed so as to obtain a catalyst; (2), adding the ortho-aminophenol, the anhydrous glycerol and the o-nitrophenol into a reactor with stirring intensely, dropping the catalyst obtained in the step 1, stirring continuously for 5 hours by maintaining the temperature at 70-90 DEG C, regulating a pH value to be 7-8 after reaction is completed, distilling to obtain crude 8-hydroxyquinoline and subjecting the crude 8-hydroxyquinoline to ethanol recrystallization so as to obtain the 8-hydroxyquinoline.The synthetic method has the advantages of higher yield of the 8-hydroxyquinoline, reduction of by-products, high purity of the 8-hydroxyquinoline, mild reaction temperature, safe preparation process and easiness for large-scale industrial production.

Description

Technical field: [0001] The invention relates to the technical field of biomedicine, in particular to an 8-hydroxyquinoline and a synthesis method thereof. Background technique: [0002] 8-Hydroxyquinoline is an important pharmaceutical intermediate and an intermediate for the preparation of halogenated quinoline anti-amoeba drugs, which has a significant effect on the treatment of amoebic dysentery. At the same time, it is also an important raw material for organic synthesis. Its sulfate and copper salts are excellent disinfectants and anti-corrosion and anti-mold agents. Using 8-hydroxyquinoline as a raw material to synthesize fuels, pesticides and dyes is a very common production method. Since 8-hydroxyquinoline has very important uses in many fields, its preparation method has been widely concerned and researched. [0003] At present, the common synthesis methods of 8-hydroxyquinoline include chlorination hydrolysis, sulfonation alkali fusion, Skraup synthesis and amin...

Claims

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Application Information

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IPC IPC(8): C07D215/26
CPCC07D215/26
Inventor 叶芳
Owner 叶芳
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