Preparation method of pyridoxal or pyridoxal hydrochloride

A technology for pyridoxal hydrochloride and pyridoxal hydrochloride, which is applied in the field of preparation of pyridoxal or pyridoxal hydrochloride, can solve the problems of large reaction pollution and complicated process, and achieves good selectivity, high conversion rate and convenient operation. Effect

Active Publication Date: 2012-08-01
ZHEJIANG UNIV OF TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In order to overcome the disadvantages of large reaction pollution and complicated process in the prior art, the purpose of the present invention is to provide a method with high conversion rate, good selectivity, mild reaction conditions, convenient operation, low cost, environmental friendliness and good industrial application The method for the selective oxidation of pyridoxine or pyridoxine hydrochloride to prepare pyridoxal or pyridoxal hydrochloride

Method used

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  • Preparation method of pyridoxal or pyridoxal hydrochloride
  • Preparation method of pyridoxal or pyridoxal hydrochloride
  • Preparation method of pyridoxal or pyridoxal hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0030] In a 25mL reaction flask with a stirrer and a thermometer, add 0.085g (0.5mmol) 2,2,6,6-tetramethylpiperidine-nitrogen-oxygen radical, 0.29g (2mmol) copper bromide successively, 0.40g (5mmol) pyridine and 2.06g (10mmol) pyridoxine hydrochloride. Add 5 mL of water, control the temperature at 30°C, and start stirring. Then 2.0 g (18 mmol) of 30% hydrogen peroxide was added dropwise while controlling the reaction temperature at 30-35° C. After the dropwise addition, keep stirring at 30-35° C. for 1-2 hours, and the obtained reaction solution detects that the pyridoxine conversion rate reaches 99% (liquid phase conditions: the chromatographic column is XDB-G8 250×4.6mm 5um. The mobile phase is methanol: buffer=15:85; buffer: 0.04% sodium pentanesulfonate and adjust the pH to 3 with glacial acetic acid; the detection wavelength is 284nm), and the reaction selectivity is 98%.

[0031] In addition, take about 5mL of the reaction solution and put it directly on the silica gel...

Embodiment 2

[0034] The oxygen source was changed to 1 atmosphere of oxygen, the inorganic salt was changed to 1.5g (10mmol) copper nitrate, the amine ligand was changed to 1.0g (10mmol) triethylamine, and other operations were the same as in Example 1 to obtain 2.21g of a yellow solid. The conversion rate of pyridoxine is up to 99% and the reaction selectivity is 97% according to liquid phase detection. The overall yield of the two-step reaction was 89%.

Embodiment 3

[0036] Oxygen source is changed into the oxygen of 2 atmospheric pressures, and inorganic salt is changed into 0.29g (2mmol) cuprous bromide, and amine ligand is changed into 0.24g (4mmol) 1,2-ethylenediamine, and other operation is with embodiment 1, 1.90 g of a yellow solid was obtained. The conversion rate of pyridoxine is up to 87% and the reaction selectivity is 95% according to liquid phase detection. The overall yield of the two-step reaction was 74%.

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Abstract

The invention discloses a preparation method of pyridoxal or pyridoxal hydrochloride. The preparation method comprises: taking pyridoxine or pyridoxine hydrochloride shown in formula (III) as the starting material and water as the reaction solvent, conducting selective oxidation on the pyridoxine or pyridoxine hydrochloride in water under the effect of a catalytic oxidation system, thus obtaining the pyridoxal or pyridoxal hydrochloride shown in formula (I). The catalytic oxidation system includes an oxygen source, a catalyst, an inorganic salt and an amine ligand. The preparation method of the invention has the advantages of high conversion rate, good selectivity, mild reaction condition, easy operation, low cost, and environmental friendliness, thus boasting good industrial application value.

Description

(1) Technical field [0001] The invention relates to a method for preparing pyridoxal or pyridoxal hydrochloride, in particular to a method for selectively oxidizing pyridoxine or pyridoxine hydrochloride to prepare pyridoxal or pyridoxal hydrochloride. (2) Background technology [0002] Pyridoxal hydrochloride is a vitamin B 6 A derivative of , as shown in formula (I), is a key intermediate for the synthesis of pyridoxal 5-phosphate. The chemical name of pyridoxal 5-phosphate is 2-methyl-3-hydroxy-4-formaldehyde-5-hydroxymethylpyridinium phosphate, referred to as PLP, which is vitamin B 6 An active ingredient formed under the action of adenosine triphosphate kinase in cells, the structural formula is as formula (II): [0003] [0004] As a coenzyme, pyridoxal 5-phosphate can interact with more than 100 different enzymes in the body to jointly affect the biochemical activities and metabolism of cells in the body. It is an essential substance to maintain the normal immun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/66
Inventor 施湘君苏为科陈巧巧章根宝
Owner ZHEJIANG UNIV OF TECH
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