Synthesis method of 2,5-bis(substituted amino)-1,4-benzoquinone compound

A disubstituted, amino technology, applied in the field of synthetic organic compounds, can solve the problems of long reaction time and low yield

Inactive Publication Date: 2011-09-28
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Synthetic methods such as Kevin W. Wellington not only have a long reaction time, the yield is generally lower than 30%, but also use expensive enzyme preparations

Method used

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  • Synthesis method of 2,5-bis(substituted amino)-1,4-benzoquinone compound
  • Synthesis method of 2,5-bis(substituted amino)-1,4-benzoquinone compound
  • Synthesis method of 2,5-bis(substituted amino)-1,4-benzoquinone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Example 1: Synthesis of 2,5-dimethylamino-1,4-benzoquinone (1).

[0029] Take 0.5g (0.00454mol) of hydroquinone and add 10ml of ethanol to dissolve it. Take 30% methylamine in ethanol solution, of which methylamine is 1.88g (0.0182mol), add 10ml of ethanol to dilute (reaction molar ratio is hydroquinone:methylamine=1:4), dilute the diluted methylamine alcohol solution Slowly drop the hydroquinone solution, the color of the mixture turns from light brown to brown. Heated in a water bath, the temperature was controlled at 55°C, and the reaction time was 3h. Track and detect the reaction with TLC, the developer is ethyl acetate: sherwood oil=5:1, R f =0.667. After 30 min of reaction, the solution turned from light red to dark red. After the reaction, a red powdery product was formed in the cooled reaction liquid. Filter to obtain crude product. Recrystallize from ethanol. Air-dried to obtain a red powdery pure product, observed under a microscope as red crystals. T...

Embodiment 2

[0030] Example 2: Synthesis of 2,5-bis(dimethylamino)-1,4-benzoquinone (2).

[0031] Take 0.5g (0.00454mol) of hydroquinone and add 10ml of ethanol to dissolve it. Weigh the aqueous solution of dimethylamine, in which dimethylamine is 2.485g (0.01816mol), add 10ml of ethanol to dilute (reaction molar ratio is hydroquinone: dimethylamine = 1:4). Slowly drop the diluted alcohol solution of dimethylamine solution into the ethanol solution of hydroquinone, and the color of the mixture changes from light brown to brown. Heated in a water bath, the temperature was controlled at 55°C, and the reaction time was 2h. TLC tracking detection reaction, the developer is ethyl acetate: petroleum ether = 5:1, R f = 0.62. After reacting for 25 min, the solution turned from brown to dark red. After the reaction was finished, it was cooled, and no solid was generated in the reaction solution, and the color of the solution was reddish black. The reaction solution was sealed and placed in the...

Embodiment 3

[0032] Example 3: Synthesis of 2,5-diethylamino-1,4-benzoquinone (3).

[0033] Take 0.5g (0.00454mol) of hydroquinone and add 10ml of ethanol to dissolve it. Weigh the ethylamine aqueous solution, in which the ethylamine is 0.584g (0.00908mol), add 10ml of ethanol to dilute (reaction molar ratio is hydroquinone:ethylamine=1:2). Slowly drop the diluted ethylamine solution into the ethanol solution of hydroquinone, and the color of the mixture changes from light brown to brown. Heated in a water bath, the temperature was controlled at 52°C, and the reaction time was 6h. TLC tracking detection, the developer is ethyl acetate:petroleum ether=5:1, R f = 0.67. After 30 min of reaction, the solution turned from light red to dark red. After the reaction was finished, it was cooled, and no solid matter was generated in the reaction liquid. Seal the reaction solution and put it in the refrigerator to cool down. The next day, bright red crystals precipitated and were filtered to obt...

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Abstract

The invention discloses a synthesis method of a 2,5-bis(substituted amino)-1,4-benzoquinone compound. The method comprises the following steps of: dissolving hydroquinone in a polar solvent, diluting aliphatic or aromatic primary amine and secondary amines with a polar solvent, dripping diluted aliphatic or aromatic primary amine and secondary amines to a hydroquinone solution to obtain a mixed solution, heating the mixed solution in a water bath and finally separating reaction liquid to obtain a product. The synthesis method provided by the invention, with inexpensive hydroquinone, aliphatic or aromatic primary amine and secondary amines as raw materials, overcomes the defect that the synthesis method in the prior art has high production cost or low yield, embodies green, energy-saving and environmental protection concepts, and has high potential application value.

Description

[0001] technical field [0002] The invention relates to a synthetic organic compound, in particular to a method for synthesizing 2,5-disubstituted amino-1,4-benzoquinone compounds. Background technique [0003] Quinones are found in many animal and plant cells and are widely used as anticancer, antibacterial, antimalarial and antifungal agents. Aminobenzoquinone is a drug for treating tumors and nematodes, and can also be used as a herbicide, and has potential anti-allergic, anti-viral and 5-lipoxygenase inhibitory activities. In 2007, Syamaprasad Bayen et al. used various primary amines and 1,4-benzoquinone as raw materials to synthesize the corresponding 2,5-bis(alk / arylamino)1,4-benzoquinone. They also synthesized the corresponding 2-amino-1,4-naphthoquinone derivatives by reacting 1,4-naphthoquinone with primary amines. In 2010, Kevin W. Wellington et al. reported that aliphatic and aromatic primary amines and p-benzoquinone were prepared under mild conditions, in ope...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/28C07C221/00
Inventor 王建刘玮炜周再伟秦玉
Owner HUAIHAI INST OF TECH
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