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Method for preparing 4-amino catechol

A technology of aminocatechol, nitrocatechol dibenzyl ether, applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., can solve the problem that 4-aminocatechol is not Problems such as the preferred method, to achieve the effect of shortening the reaction steps, mild reaction conditions and high reaction yield

Inactive Publication Date: 2013-03-20
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the yield of this route is as high as 95%, the raw material is difficult to obtain and is not suitable for industrial production;
[0017] (4) Route 4 uses catechol as raw material and nitrates to obtain 3-nitrocatechol, 4-nitrocatechol and 3, 4-Dinitrocatechol, etc., the product is complex, high boiling point, difficult to separate
[0024] In summary, the current methods for preparing 4-aminocatechol are not the best methods

Method used

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  • Method for preparing 4-amino catechol
  • Method for preparing 4-amino catechol
  • Method for preparing 4-amino catechol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the preparation of pyrocatechol dibenzyl ether ：

[0040] Add 10.00 g (0.091 mol) catechol to a 250 mL three-neck flask, 37.60 g (0.272 mol) K 2 CO 3 and 50 mL DMF, stirred, then added 27.58 g (0.218mol) benzyl chloride, heated to 125 °C, reacted for 2 h, TLC (petroleum ether: ethyl acetate = 6: 1, Rf = 0.6) to detect the reaction end point, to be reacted The solution was cooled to room temperature, 120 mL of water was added to the reaction system, stirred, and the solid was collected by filtration, washed with water, and dried to obtain 25.68 g of catechol dibenzyl ether, with a yield of 97%.

[0041] Catechol dibenzyl ether: 1 H NMR (400 MHz, CDCl 3 , δ, ppm): 5.17 (s, 4H, CH 2), 6.87~6.90 (m, 2H, aromatics), 6.93~6.96 (m, 2H, aromatics), 7.28~7.31 (m, 2H, aromatics), 7.34~7.38 (t, 4H, J 1 = 7.6 Hz, J 2 = 6.8 Hz, aromatics), 7.45 (d, 4H, J= 7.2 Hz, aromatics); IR (KBr, cm -1 ): 3059, 3024, 2939, 1589, 1505, 1451, 1207, 1002, 742, 696.

[0042] ...

Embodiment 2

[0043] Embodiment 2: the preparation of 4-nitrocatechol dibenzyl ether:

[0044] Add 1.01 g (0.0034 mol) catechol dibenzyl ether and 15 mL glacial acetic acid into a 100 mL three-necked flask, and add 2 drops of concentrated H 2 SO 4 , stirred at room temperature to dissolve. Add dropwise from 0.33 g (0.0034 mol) 65%HNO 3 and 5 mL of glacial acetic acid, the addition was completed in about 1 h, and the reaction was continued for about 0.5 h. TLC (petroleum ether: ethyl acetate = 6: 1, Rf = 0.5) was used to detect the reaction end point, and 40 mL of ice was added to the reaction bottle water, stirred, allowed to stand, and the solid was collected by filtration, washed with water until neutral, and dried to obtain 1.09 g of 4-nitrocatechol dibenzyl ether, with a yield of 94%.

[0045] 4-nitrocatechol dibenzyl ether: 1 H NMR (400 MHz, CDCl 3 , δ, ppm): 5.25 (d, 4H, J= 17.2 Hz, CH 2 ), 5.95 (d, 1H, J= 8.8 Hz, aromatic), 7.32~7.48 (m, 10H, aromatics), 7.83 (d, 1H, J= 2.8 Hz...

Embodiment 3

[0047] Embodiment 3: the preparation of 4-aminocatechol:

[0048] Add 0.51 g (0.0015 mol) 4-nitrocatechol dibenzyl ether and 20 mL ethyl acetate to a 100 mL single-necked bottle, add 0.05 g Pd / C after dissolution, and then adjust the reaction temperature to 35~40 °C , into H 2 Until the reaction system no longer absorbs gas, TLC (petroleum ether: ethyl acetate=1:5, Rf=0.4) detects the end point of the reaction, collects the liquid by filtration, evaporates the solvent under reduced pressure, and obtains 0.17 g of the white target product, the yield 90%.

[0049] 4-Aminocatechol: 1 H NMR (400 MHz, DMSO, δ, ppm): 4.37 (br s 2H, NH 2 ), 5.84 (d, 1H, J= 8 Hz, aromatic), 6.06 (s, 1H, aromatic), 6.40 (d, 1H, J= 8 Hz, aromatic), 7.75 (s, 1H, OH), 8.41 ( s, 1H, OH); IR (KBr, cm -1 ): 3361, 3292, 1610, 1527, 1471, 1372, 1259, 1202, 889, 802.

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Abstract

The invention relates to a method for preparing 4-amino catechol by three-step reaction synthesis by taking catechol as raw material; compared with the existing method for preparing the 4-amino catechol, the method has the advantages of being mild in reaction conditions, low in price and easy in the obtain of raw materials, high in yield and low in pollution to the environment, having the total yield of the three-step reaction reaching up to 80%, and the like; therefore, the method is more suitable for industrial production and is good for preparing the 4-amino catechol.

Description

technical field [0001] The invention relates to a new synthesis process of 4-aminocatechol. Background technique [0002] 4-Aminocatechol is an important intermediate in the synthesis of a retinoid derivative. Retinoids are a class of natural medicines containing electron-rich conjugated systems, which have many pharmacological effects such as good lipophilicity, inhibition of tumor occurrence, and inhibition of cancer cell proliferation and spread. At present, in order to obtain new-type retinoid prodrugs with high efficiency and low toxicity, medicinal chemists have carried out a lot of research work and achieved some research results. Among them, Um. Soo-Jong et al. Diphenols were used as intermediates to synthesize a series of derivatives with anticancer activity. Therefore, it is of practical application value to study the synthetic method of 4-aminocatechol. [0003] The existing method of synthesizing 4-aminocatechol is as follows: [0004] 1. Obtain 4-aminocatech...

Claims

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Application Information

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IPC IPC(8): C07C213/02C07C215/78
Inventor 吴凯群罗茜王玉良
Owner SICHUAN UNIV
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