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Preparation method for synthesizing pyrroloquinoline quinone by four-step method

A technology of pyrroloquinoline quinone and four-step method, which is applied in organic chemistry and other fields, can solve the problems of high preparation cost, large environmental pollution, and difficult industrial production, and achieve the effect of simple method, environmental friendliness, and wide sources

Pending Publication Date: 2020-05-01
JIANGXI AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The object of the present invention is to provide a kind of preparation method of the pyrroloquinoline quinone that is green, pollution-free, environment-friendly, raw material is easy to get, source is wide, cost is low, method is simple, is suitable for industrialized production, and this preparation method solves the problem of existing The problems of high preparation cost, high environmental pollution and difficulty in industrial production in the technology

Method used

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  • Preparation method for synthesizing pyrroloquinoline quinone by four-step method

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Experimental program
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Effect test

Embodiment 1

[0018] The preparation method of pyrroloquinoline quinone: 4-methyl-5-nitro-2-fluoroaniline (2) (170.14 g, 1.00 mol), 1,2-dichloroethane (1.00 L), 4-oxo Diethyl-2-enylglutarate (200.19 g, 1.00 mol) and concentrated hydrochloric acid (8 mL, 0.1 mol) were placed in a three-necked flask, and heated to reflux for 5 h. After the reaction was cooled, the liquids were separated and dried. The solvent was recovered under reduced pressure to obtain the crude product 6-methyl-5-nitro-8-fluoroquinoline-2,4-dicarboxylic acid diethyl ester (3); compound 3, diethyl oxalate (146.14 g, 1.00 mol), sodium methoxide (54.02 g, 1.00 mol) and methanol (1.00 L) were placed in a three-necked flask, heated to reflux for 5 h, and after the reaction was cooled, filtered to obtain 6-(2-ethoxycarbonyl-2-oxo Diethyl)-5-nitro-8-methoxyquinoline-2,4-dicarboxylate (5) in methanol; compound 5 in methanol and 5% palladium on carbon (2 g) Place in a high-pressure reactor, fill with hydrogen, keep the pressure a...

Embodiment 2

[0020] The preparation method of pyrroloquinoline quinone: 4-methyl-5-nitro-2-fluoroaniline (2) (170.14 g, 1.00 mol), dichloromethane (1.00 L), 4-oxo-2-ene Dimethyl glutarate (172.14 g, 1.00 mol) and 5 M dilute sulfuric acid (20 mL, 0.1 mol) were placed in a three-neck flask, heated to reflux for 5 h, after the reaction was cooled, separated, dried, and recovered under reduced pressure solvent to obtain crude 6-methyl-5-nitro-8-fluoroquinoline-2,4-dicarboxylic acid dimethyl ester (3); compound 3, dimethyl oxalate (118.09 g, 1.00 mol), Sodium carbonate (212.00 g, 2.00 mol) and methanol (1.00 L) were placed in a three-necked flask, heated to reflux for 5 h, and after the reaction was cooled, filtered to obtain 6-(2-methoxycarbonyl-2-oxoethyl )-5-nitro-8-methoxyquinoline-2,4-dicarboxylate (5) in methanol; compound 5 in methanol and Raney nickel (5 g) were subjected to high pressure reaction In the kettle, fill with hydrogen, keep the pressure of 5 atmospheres, heat to 50 ° C, re...

Embodiment 3

[0022] The preparation method of pyrroloquinoline quinone: 4-methyl-5-nitro-2-fluoroaniline (2) (170.14 g, 1.00 mol), benzene (1.00 L), 4-oxo-2-pentadiene Acetate dibenzyl ester (324.33 g, 1.00 mol) and methanesulfonic acid (9.61 g, 0.1 mol) were placed in a three-necked flask, and heated to reflux for 5 h. After the reaction was cooled, the liquid was separated, dried, and the solvent was recovered under reduced pressure to obtain Crude dibenzyl 6-methyl-5-nitro-8-fluoroquinoline-2,4-dicarboxylate (3); compound 3, dibenzyl oxalate (270.28 g, 1.00 mol), potassium carbonate (276.00 g, 2.00 mol) and methanol (1.00 L) were placed in a three-necked flask, heated to reflux for 5 h, and after the reaction was cooled, filtered to obtain 6-(2-benzyloxycarbonyl-2-oxoethyl)- Dibenzyl 5-nitro-8-methoxyquinoline-2,4-dicarboxylate (5) in methanol; compound 5 in methanol and 20% platinum on carbon (5 g) were placed in an autoclave , filled with hydrogen, kept at a pressure of 5 atmospheres...

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Abstract

The invention discloses a preparation method for synthesizing pyrroloquinoline quinone by a four-step method. According to the method, 4-methyl-5-nitro-2-fluoroaniline (2) is taken as a raw material,and is subjected to a ring closing reaction twice to obtain a key intermediate 5-methoxy-1H-pyrrole [2,3-f] quinoline-2,7,9-trialkyl triformate (6), and an oxidation reaction, a hydrolysis reaction and an acidification reaction are performed to obtain the pyrroloquinoline quinone (PQQ, 1). The preparation method disclosed by the invention has the advantages of environmental friendliness, easily available raw materials, low cost, simple method and suitability for industrial production, and solves the problems of high preparation cost and difficulty in industrial production in the prior art.

Description

technical field [0001] The invention relates to the field of organic synthetic chemistry, in particular to a preparation method for synthesizing pyrroloquinoline quinone by a four-step method. Background technique [0002] Pyrroloquinoline quinone (PQQ) is a new coenzyme of oxidoreductase discovered in the late 1970s. + 、NADP + ) after the third enzyme discovered. As an oxidoreductase prosthetic group, PQQ exists in almost all biological tissues and is a new type of water-soluble vitamin. Studies have shown that PQQ has some important functions: stimulating the growth of microorganisms, promoting the synthesis of nerve growth factors, essential factors for animal growth and development, etc. Therefore, it is of great theoretical and practical significance to study the synthesis and production of pyrroloquinoline quinone that is non-polluting, readily available and inexpensive. Contents of the invention [0003] The object of the present invention is to provide a kind o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 黄建平黄国平黄剑雄黄喜根蔡军火方文超黄川应俊杰余荣静
Owner JIANGXI AGRICULTURAL UNIVERSITY
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