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Preparation method of 3-chloro-2-aminophenol

A technology of aminophenol and chlorophenol, which is applied in the field of medicine and chemical industry, can solve the problems of poor purity, low product yield, and low final product yield, and achieve the effects of high product purity and yield, high yield, and mild reaction

Active Publication Date: 2015-07-08
LINHAI LIANSHENG CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the present methods for synthesizing 3-chloro-2-aminophenol, most of them have problems such as low yield or poor purity of the final product
For example, it is disclosed that 3-chloro-2-nitrophenol is used as a raw material to react under tin powder and acidic medium to obtain 3-chloro-2-aminophenol, but there are problems such as low product yield in this method

Method used

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  • Preparation method of 3-chloro-2-aminophenol
  • Preparation method of 3-chloro-2-aminophenol
  • Preparation method of 3-chloro-2-aminophenol

Examples

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Embodiment 1

[0030] Add 10 g of m-chlorophenol, 60 mL of acetic acid, and then, 5 mL of concentrated HNO 3 Dilute in 20 mL of acetic acid solution, and slowly dissolve HNO at -5°C to 5°C 3 The mixture of acetic acid and acetic acid was dropped into the flask. After the dropwise addition, the temperature was slowly raised to 20°C, and the temperature was controlled to carry out the stirring substitution reaction for 15 hours. After the reaction, concentrated under reduced pressure to remove acetic acid, and then added ethyl acetate to the residue Washing and extraction with saturated sodium chloride solution were repeated three times, and the collected organic phase was concentrated under reduced pressure to remove the solvent, and then purified through the column. The mobile phase used in the column was petroleum ether, dichloromethane and ethyl acetate and the volume ratio of petroleum ether: dichloromethane: ethyl acetate was 20:1:1, and 3.19 g of yellow solid 3-chloro-2-nitrophenol was ...

Embodiment ２

[0039] Add 10 g of m-chlorophenol, 40 mL of acetic acid, and then, 5 mL of concentrated HNO 3 Dilute in 20 mL of acetic acid solution, and slowly dissolve HNO in an ice bath 3 The mixed solution of acetic acid / acetic acid was dropped into the flask. After the dropwise addition, it was naturally raised to room temperature, and the temperature was controlled to carry out the stirring substitution reaction for 12 hours. After the reaction was completed, it was concentrated under reduced pressure to remove acetic acid, and then ethyl acetate and Saturated sodium chloride solution was washed, extracted, and repeated three times. After the collected organic phase was concentrated under reduced pressure to remove the solvent, it was purified through the column. The mobile phase used in the column was petroleum ether, dichloromethane and ethyl acetate. The mobile phase was mixed, and the volume ratio of petroleum ether: dichloromethane: ethyl acetate was 1:1:20 to obtain 2.70 g of yel...

Embodiment ３

[0042] Add 10 g of m-chlorophenol, 70 mL of acetic acid, and then, 5 mL of concentrated HNO 3 Dilute in 20 mL of acetic acid solution, and slowly dissolve HNO at -5°C to 5°C 3 The mixture of acetic acid and acetic acid was dropped into the flask. After the dropwise addition, the temperature was slowly raised to 30°C, and the temperature was controlled to carry out the substitution reaction with stirring for 10 hours. After the reaction, concentrated under reduced pressure to remove acetic acid, and then added ethyl acetate to the residue Washing and extraction with saturated sodium chloride solution were repeated three times, and the collected organic phase was concentrated under reduced pressure to remove the solvent, and then purified through the column. The mobile phase used in the column was petroleum ether, dichloromethane and ethyl acetate and the volume ratio of petroleum ether:dichloromethane:ethyl acetate (mL / mL / mL) is 20:1:1 to obtain 2.97g of yellow solid 3-chloro-2...

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Abstract

The invention relates to a preparation method of 3-chloro-2-aminophenol, belonging to the technical field of pharmaceutical chemicals. The method comprises the following steps of: subjecting m-chlorophenol and concentrated HNO3 to substitution reaction in an acetate solvent, after the reaction is ended, removing the solvent, and then, carrying out column purification to obtain 3-chloro-2-nitrophenol; and then, adding the 3-chloro-2-nitrophenol and hydrazine hydrate in a mixed solvent of alcohol and water in the existence of ferrous sulfate to carry out reduction reaction to obtain a final product, namely the 3-chloro-2-aminophenol. The preparation method has the advantages of simple process, high product purity and high yield; and acetate is used as the solvent which not only can play a role as a reaction solvent for ensuring more mild reaction, but also can play a role as a catalyst for ensuring the success of the reaction.

Description

technical field [0001] The invention relates to a preparation method of 3-chloro-2-aminophenol, which belongs to the technical field of medicine and chemical industry. Background technique [0002] Halogenated 2-aminophenols are mainly used in industrial fields such as dyes and medicines. Among dyes, 4-chloro-2-aminophenols are the main intermediates for the synthesis of acidic medium brown RH and acidic complex violet 5RH. In the field of medicine, for example, 3-chloro-2-aminophenol can be used as synthetic marine biological products and so on. Therefore, halogenated 2-aminophenols have a wide range of applications, especially 3-chloro-2-aminophenols, which have good research prospects. However, most of the current methods for synthesizing 3-chloro-2-aminophenol have problems such as low yield or poor purity of the final product. For example, it is disclosed that 3-chloro-2-nitrophenol is used as a raw material to react under tin powder and acidic medium to obtain 3-chlo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/76C07C213/02C07D213/40
Inventor 周其忠张斌蒋华江陈仁尔俞小鸥
Owner LINHAI LIANSHENG CHEM
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