Method for preparing 6-hydroxy-2(1H)-quinolone in ionic liquid by using one-pot method

A technology of ionic liquids and quinolinones, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problem of increasing operational complexity, affecting the industrial application of Heck reaction, and complicated separation Process and other issues, to achieve the effect of reducing loss and waste generation, good reusability performance, and improving reaction yield

Inactive Publication Date: 2011-04-27
JIANGSU FOOD SCI COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (3) Gattermann used electrochemical method to reduce the nitro group of 2-nitro-5-hydroxycinnamic acid to amino group, and then carried out ring-forming reaction. The method is limited by production cost, production equipment and production scale, so it is difficult to promote and apply in our country at present
[0007] (4) Richard started from N-oxidized-6-methoxyquinoline, chlorination, methoxylation and acidification , the reaction process involves a complicated separation process, and the product yield is low
The traditional Heck reaction usually uses Pd(0) as a catalyst, which requires an equal or multiple amount of ligand, and the reaction is sensitive to air and water, and needs to be carried out under the protection of an inert gas, which increases the complexity of the operation and affects The Industrial Application of Heck Reaction
Homogeneous catalysts such as PdCl2 or Pd(OAc)2 can effectively catalyze the Heck reaction, but they are difficult to separate and recycle from the reaction system. It is easy to generate palladium black in the medium, which not only reduces the activity of the catalyst, but also contaminates the reaction product.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Ionic liquid [bmim]Br 3 Preparation: Add 3 mol of 1-methylimidazole and 0.9 L of toluene into a 2.5 L reactor, add 3 mol of 1-bromobutane dropwise under stirring, heat and reflux for 12 h; cool, separate the toluene layer, Wash with ethyl acetate and chloroform, and dry under vacuum at 80°C for 48 h to obtain the ionic liquid 1-butyl-3-methylimidazole bromide ([bmim]Br); add bromine dropwise to the ionic liquid [bmim]Br 3 mol, stirred and reacted at room temperature for 2 h; washed twice with 0.6L ethyl acetate and dried in vacuo to obtain the ionic liquid 1-butyl-3-methylimidazole tribromide ([bmim]Br 3 );

[0029] (2) 6-hydroxy-2( 1H One-pot synthesis of )-quinolinone: add 1 mol of p-methoxyaniline and 1 mol of ionic liquid [bmim]Br into the reactor 3 , stirred and reacted at 20°C for 30 minutes; added 0.60mol of potassium carbonate, slowly added dropwise 1.00mol of acryloyl chloride under stirring, and the dripping was completed in 30 minutes, and continued t...

Embodiment 2

[0033] (1) Ionic liquid [bmim]Br 3 Preparation: Add 3 mol of 1-methylimidazole and 0.9 L of toluene into a 2.5 L reactor, add 3 mol of 1-bromobutane dropwise under stirring, heat and reflux for 12 h; cool, separate the toluene layer, Wash with ethyl acetate and chloroform, and dry under vacuum at 80°C for 48 h to obtain the ionic liquid 1-butyl-3-methylimidazole bromide ([bmim]Br); add bromine dropwise to the ionic liquid [bmim]Br 3 mol, stirred and reacted at room temperature for 2 h; washed twice with 0.6L ethyl acetate and dried in vacuo to obtain the ionic liquid 1-butyl-3-methylimidazole tribromide ([bmim]Br 3 );

[0034] (2) 6-hydroxy-2( 1H One-pot synthesis of )-quinolinone: add 1 mol p-methoxyaniline and 0.9 mol ionic liquid [bmim]Br to the reactor 3 , stirred and reacted at 25°C for 35 minutes; added 0.7mol of potassium carbonate, slowly added 1.1mol of acryloyl chloride dropwise under stirring, and the dripping was completed in 40 minutes, and continued to stir a...

Embodiment 3

[0038] (1) Ionic liquid [bmim]Br 3 Preparation: Add 3 mol of 1-methylimidazole and 0.9 L of toluene into a 2.5 L reactor, add 3 mol of 1-bromobutane dropwise under stirring, heat and reflux for 12 h; cool, separate the toluene layer, Wash with ethyl acetate and chloroform, and dry under vacuum at 80°C for 48 h to obtain the ionic liquid 1-butyl-3-methylimidazole bromide ([bmim]Br); add bromine dropwise to the ionic liquid [bmim]Br 3 mol, stirred and reacted at room temperature for 2 h; washed twice with 0.6L ethyl acetate and dried in vacuo to obtain the ionic liquid 1-butyl-3-methylimidazole tribromide ([bmim]Br 3 );

[0039] (2) 6-hydroxy-2( 1H One-pot synthesis of )-quinolinone: add 1 mol p-methoxyaniline and 1.1 mol ionic liquid [bmim]Br to the reactor 3 , stirred and reacted at 15°C for 25 min; added 0.5 mol of potassium carbonate, slowly added dropwise 0.9 mol of acryloyl chloride under stirring, and the drop was completed in 25 min, and continued to stir and react a...

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Abstract

The invention discloses a method for preparing 6-hydroxy-2(1H)-quinolone in ionic liquid by using a one-pot method. The invention synthesizes the 6-hydroxy-2(1H)-quinolone by through bromination, acidation and intramolecular Heck reaction of p-methoxy aniline and acryloyl chloride as raw materials in the ionic liquid by using the one-pot method. The method has simple synthesis line, low product cost and high yield, is environmental friendly and is easy to realize industrial production.

Description

technical field [0001] The present invention relates to 6-hydroxyl-2( 1H The preparation method of )-quinolinone, be specifically related to a kind of one-pot method preparation 6-hydroxyl-2( 1H )-quinolinone method. Background technique [0002] 6-Hydroxy-2(1H)-quinolinone and its derivatives have antibacterial and positive inotropic activity, and are important intermediates in the synthesis of drugs for strengthening the heart, lowering blood pressure, treating diabetes, promoting cerebral circulation, anti-asthma and anti-ulcer. Since the 1980s, the research on the synthesis of cardiovascular drugs from these compounds has attracted people's attention, and many new drugs synthesized from them have entered the stage of clinical trials. Therefore, it is of great significance to study the synthesis and application of this kind of compounds. [0003] 6-Hydroxy-2(1 H )-quinolinone synthetic method mainly contains: [0004] (1) With 6-methoxyquinoline as starting material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/22B01J31/24
Inventor 袁加程刘长春
Owner JIANGSU FOOD SCI COLLEGE
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