Method of synthesizing 8-hydroxyquinoline

A hydroxyquinoline and chelate technology, applied in the field of synthesizing 8-hydroxyquinoline, can solve the problems of being unsuitable for large-scale industrial production, difficult to control the reduction degree, unstable product yield and the like, and achieve easy control of the reaction process, The effect of stable yield and simple post-processing

Active Publication Date: 2018-12-21
连云港德洋化工有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] Among the four methods, the raw materials of chloroquinoline hydrolysis and aminoquinoline hydrolysis are difficult to obtain, and are only valuable when preparing some 8-hydroxyquinoline derivatives containing special structures, and are not suitable for large-scale industrial production; quinoline Sulfonated alkali fusion, quinoline resources are limited, the sulfonation-alkali fusion method consumes a lot of raw materials and high production costs; the Skraup method uses o-aminophenol and acrolein as raw materials, and o-nitrophenol as an oxidant to synthesize 8-hydroxyquinoline, just as In 2007, our research group reported in "Synthesis of 8-Hydroxyquinoline by Skraup Method" in Volume 24, Issue 1 of "Fine Petrochemical Industry": using o-aminophenol and acrolein as raw materials and o-nitrophenol as oxidant to obtain the target product in one pot 8-hydroxyquinoline, in the reaction system, o-nitrophenol dehydrogenates the intermediate obtained by addition and cyclization of o-aminophenol and acrolein to 8-hydr...

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  • Method of synthesizing 8-hydroxyquinoline
  • Method of synthesizing 8-hydroxyquinoline
  • Method of synthesizing 8-hydroxyquinoline

Examples

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Effect test

example 1

[0039] Mix 45mL (1.5mol) hydrochloric acid, 3.3mL (0.6mol) glacial acetic acid, and 19.6g (0.18mol) o-aminophenol, stir and heat to 95-100°C, dissolve 1.0g hydroquinone in 12.0g (0.21mol) After acrolein, pour it into a constant pressure dropping funnel with a glass dropper connected to the lower end of the funnel, and slowly add it dropwise to below the liquid level of the reaction solution within 3 hours. It is measured that the filtrate only contains 18.4% of 8-hydroxyquinoline, which is directly used for the next photocatalytic dehydrogenation reaction without separation.

[0040] Add 3.0g (7.4mol×10 -3 mol)[PyCo(dmg) 2 Cl], 3.0g (4.3×10 -3 mol) Eosin Y, 50.0mL (0.96mol) of acetonitrile and 50mL (2.8mol) of deionized water, stirred, irradiated continuously with a 10W white LED lamp, and reacted at room temperature for 3 hours. After the reaction was completed, the acetonitrile was collected by vacuum distillation for reuse. Filtration, the filtrate is adjusted to pH=7, a...

example 2

[0042]Mix 45mL (1.5mol) hydrochloric acid, 3.3mL (0.6mol) glacial acetic acid, and 19.6g (0.18mol) o-aminophenol, stir and heat to 95-100°C, dissolve 1.0g hydroquinone in 12.0g (0.21mol) After acrolein, pour it into a constant pressure dropping funnel with a glass dropper connected to the lower end of the funnel, and slowly add it dropwise to below the liquid level of the reaction solution within 3 hours. Add 3.0g (7.4mol×10 -3 mol)[PyCo(dmg) 2 Cl], 3.0g (4.3×10 -3 mol) Eosin Y, 50.0mL (0.96mol) of acetonitrile and 50mL (2.8mol) of deionized water, stirred, continuously irradiated with a 10W white light LED lamp, reacted at room temperature for 3h, the reaction was completed, the reaction was completed, and the acetonitrile was collected by vacuum distillation Reuse, filter, add deionized water to the filtrate, steam distillation at normal pressure, collect the fraction at 97°C until the distillate has no white precipitate, distill the obtained filtrate to remove water under...

example 3

[0044] Mix 45mL (1.5mol) hydrochloric acid, 3.3mL (0.6mol) glacial acetic acid, and 19.6g (0.18mol) o-aminophenol, stir and heat to 95-100°C, dissolve 1.0g hydroquinone in 12.0g (0.21mol) After acrolein, pour it into a constant pressure dropping funnel with a glass dropper connected to the lower end of the funnel, and slowly add it dropwise to below the liquid level of the reaction solution within 3 hours. Add 0.5g (1.2mol×10 -3 mol)[PyCo(dmg) 2 Cl], 0.5g (7.2×10 -4 mol) Eosin Y, 50.0mL (0.96mol) of acetonitrile and 56g of the distilled raffinate of Example 1, stirred, continuously irradiated with a 10W white light LED lamp, and reacted at room temperature for 3h. , the filtrate is adjusted to pH=7, and the suction filtration filter cake under reduced pressure is a thick product, and the filtrate is distilled under reduced pressure to remove water. For the next photocatalytic reaction. The crude product was distilled under reduced pressure, the vacuum pump negative pressur...

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Abstract

The invention discloses a method of synthesizing 8-hydroxyquinoline. Ortho-aminophenol and acrolein are used as raw materials, and hydroquinone is used as a polymerization inhibitor; an addition reaction and a cyclization reaction are carried out under the acidic condition to obtain an intermediate, and a cobalt oxime chelate photocatalyst and an eosin Y photosensitizer are directly added withoutthe need of separation of the intermediate; and an acetonitrile solvent and deionized water are added, under continuous irradiation of visible light, the 8-hydroxyquinoline is obtained through a photocatalytic dehydrogenation oxidation reaction. The reaction process is easy to control, by-products are few, post-treatment is simple, and the generated target product is good in selectivity, high in yield and stable.

Description

technical field [0001] The invention belongs to the field of synthesis of organic intermediates, in particular to a method for synthesizing 8-hydroxyquinoline. Background technique [0002] 8-Hydroxyquinoline is an important intermediate in fine organic synthesis. Its synthesis process, preparation of derivatives, and biological activity are research hotspots in chemistry and medicine. With titration indicators, fluorescent reagents, 8-Hydroxyquinoline and 7-Alkyl Derivatives are metal ion extractants in the metallurgical industry. The complexes formed by its aldehyde derivative Schiff base and many kinds of metal ions have good optical activity, catalytic activity, biological activity and certain anticancer effect. , fluorescent materials and other important intermediates of functional materials, agricultural insecticides and preservatives, textiles, leather, paper, plastics and coatings as preservatives, fungicides and antifungal agents, therefore, 8-hydroxyquinoline The ...

Claims

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Application Information

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IPC IPC(8): C07D215/26
CPCC07D215/26
Inventor 张珍明李树安占垚陈达王昊宇刘义德孙成全
Owner 连云港德洋化工有限公司
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