Preparation method for synthesizing pyrroloquinoline quinone by five-step method

A technology of pyrroloquinoline quinone and one-step method is applied in the field of preparation of five-step method for synthesizing pyrroloquinoline quinone, and can solve the problems of large environmental pollution, high preparation cost, difficult industrialized production and the like

Pending Publication Date: 2020-04-10
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

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

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Experimental program
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Effect test

Embodiment 1

[0023] 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 carbonate (212.00 g, 2.00 mol) and tetrahydrofuran (1.00 L) were placed in a three-necked flask, heated to reflux for 5 hours, after the reaction was cooled, filtered, and the solvent was recovered under reduced pressure to obtain the crude product 6-(2-ethoxy Carbonyl-2-oxoethyl)-5-nitro-8-fluoroquinoline-2,4-dicarboxylate (5); compound 5, 5% palladium on carbon (2 g) and methanol (1.00 L) w...

Embodiment 2

[0025] 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), Potassium carbonate (276.00 g, 2.00 mol) and 2-methyltetrahydrofuran (1.00 L) were placed in a three-necked flask, heated to reflux for 5 h, after the reaction was cooled, filtered, and the solvent was recovered under reduced pressure to obtain the crude product 6-(2-methanol Oxycarbonyl-2-oxoethyl)-5-nitro-8-fluoroquinoline-2,4-dicarboxylic acid dimethyl ester (5); compound 5, Raney nickel (5 g) and methanol (1.00 L) was placed in a high-pressu...

Embodiment 3

[0027]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 Acid dibenzyl ester (324.33 g, 1.00 mol) and methanesulfonic acid (9.61 g, 0.1 mol) were placed in a three-necked flask, heated to reflux for 5 h, after the reaction was cooled, washed with water, separated, and dried to obtain 6-methyl Dibenzyl-5-nitro-8-fluoroquinoline-2,4-dicarboxylate (3) in benzene; compound 3 in benzene, dibenzyl oxalate (270.28 g, 1.00 mol) and Sodium hydroxide (40.00 g, 1.00 mol) was placed in a three-necked flask, and heated to reflux for 5 h. After the reaction was cooled, the solvent was recovered under reduced pressure to obtain the crude product 6-(2-benzyloxycarbonyl-2-oxoethyl) -Dibenzyl 5-nitro-8-fluoroquinoline-2,4-dicarboxylate (5); put compound 5, 20% platinum on carbon (5 g) and ethanol (1.00 L) in an autoclave , filled with hydrogen, kept the pressure of 5 atmospheres, heated to 50 ℃, re...

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Abstract

The intention discloses a preparation method for synthesizing pyrroloquinoline quinone by a five-step method, and the method comprises the following steps: by using 4-methyl-5-nitro-2-fluoroaniline (2) as a raw material, carrying out cyclization reaction twice to obtain a key intermediate 5-fluoro-1H-pyrrole [2, 3-f] quinoline-2, 7, 9-triformatetrialkyl ester (6); and carrying out hydrolysis reaction, substitution reaction and oxidation reaction to obtain pyrroloquinoline quinone (PQQ, 1). The preparation method has the advantages of greenness, environmental friendliness, easily available rawmaterial, 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 five-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 黄建平黄国平黄喜根蔡军火方文超黄川彭官威邹柳红
Owner JIANGXI AGRICULTURAL UNIVERSITY
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