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A kind of synthetic method of 3-amino-2-hydroxyacetophenone

A technology for hydroxyacetophenone and a synthesis method, which is applied in chemical instruments and methods, preparation of nitro compounds, preparation of organic compounds, etc., can solve the problems of low number of times of catalyst recovery, long reaction time, explosion safety and the like, and achieve control High temperature degradation of impurity generation, long reaction time and high space-time efficiency

Active Publication Date: 2020-06-02
HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In order to solve the problems of low yield, low purity, prone to violent explosions and potential safety hazards caused by the above-mentioned two-step reaction in traditional process operation equipment, degradation caused by long reaction time at high temperature, and low number of times of catalyst recovery and application, the present invention aims to solve the following problems: The technical problem is to provide an intrinsically safe and environmentally friendly 3-amino-2-hydroxyacetophenone synthesis technology

Method used

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  • A kind of synthetic method of 3-amino-2-hydroxyacetophenone
  • A kind of synthetic method of 3-amino-2-hydroxyacetophenone
  • A kind of synthetic method of 3-amino-2-hydroxyacetophenone

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Effect test

Embodiment 1

[0045] Weigh 180.00g of 2-hydroxy-5-chloroacetophenone and add it to 1200ml of glacial acetic acid to form material I after stirring and dissolving, weigh 100g of fuming nitric acid and add it to 800ml of glacial acetic acid to form material II, and adjust the flow rate of metering pump A Make the flow velocity of material I be 15ml / min, the flow velocity of regulating metering pump B makes the flow velocity of material II be 7ml / min, temperature of reaction is 65 ℃, and the mol ratio of nitric acid and 2-hydroxyl-5-chloroacetophenone is 1.5: 1. The residence time of the reaction is 95 seconds. Collect the reaction solution flowing out from the outlet, measure 3600ml of water and slowly drop it into the reaction system, a large amount of yellow solid precipitates, keep stirring at room temperature for 1h, filter, and add 500ml of cold ethanol to the filter cake to wash. Vacuum drying at 50°C for 6 hours gave 207.76 g of 2-hydroxy-3-nitro-5-chloroacetophenone with a yield of 91....

Embodiment 2

[0048] Weigh 150.00g of 2-hydroxyl-5-chloroacetophenone and add it into 1000ml of glacial acetic acid to form material I after stirring and dissolving; take 92g of found nitric acid and add it into 500ml of glacial acetic acid to form material II; adjust the flow rate of metering pump A to The flow rate of material I is 18ml / min, adjust the flow rate of metering pump B so that the flow rate of material II is 9ml / min, the reaction temperature is 60°C, and the molar ratio of nitric acid to 2-hydroxy-5-chloroacetophenone is 1.5:1 , the residence time of the reaction is 75 seconds, collect the reaction solution flowing out from the outlet, measure 3000ml of water and slowly drop it into the reaction system, a large amount of yellow solid is precipitated, stirred at room temperature for 1h, filtered, and the filter cake was washed with 450ml of cold ethanol, 50 Vacuum drying at °C for 6 hours gave 171.73 g of 2-hydroxy-3-nitro-5-chloroacetophenone with a yield of 90.59% and a purity...

Embodiment 3

[0051] Weigh 200.00g of 2-hydroxy-5-chloroacetophenone and add it to 1600ml of glacial acetic acid to form material I after stirring and dissolving. Weigh 100g of fuming nitric acid and add it to 800ml of glacial acetic acid to form material II. Adjust the flow rate of metering pump A Make the flow velocity of material I be 12ml / min, the flow velocity of regulating metering pump B makes the flow velocity of material II be 6ml / min, temperature of reaction is 70 ℃, and the mol ratio of nitric acid and 2-hydroxyl-5-chloroacetophenone is 1.2: 1. The residence time of the reaction is 100 seconds. Collect the reaction solution flowing out from the outlet, measure 4800ml of water and slowly drop it into the reaction system, a large amount of yellow solids will precipitate, keep stirring at room temperature for 1 hour, filter, and add 600ml of cold ethanol to the filter cake to wash. Vacuum drying at 50°C for 6 hours gave 229.63 g of 2-hydroxy-3-nitro-5-chloroacetophenone with a yield ...

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Abstract

The invention provides a synthesis method of 3-amino-2-hydroxyacetophenone.The synthesis method comprises the following steps: dissolving 2-hydroxy-5-chloroacetophenone in glacial acetic acid, dissolving fuming nitric acid in glacial acetic acid, mixing the two solutions in a micro-channel reactor to react to generate a product; dissolving the product and triethylamine in solvent and then adding active carbon loading 10%(w / w) Pd to obtain a reaction product, allowing the reaction product to react with hydrogen in the micro-channel reactor to generate 2-hydroxy-3-aminoacetophenone. The method has the advantages of high yield, high purity, rapid and accurate control, continuous production and high safety.

Description

technical field [0001] The invention belongs to the field of synthesis of anti-asthma and anti-allergic drugs in organic synthesis, and specifically relates to a synthesis method of 3-amino-2-hydroxyacetophenone. Background technique [0002] Prenz is the world's first leukotriene receptor antagonist pioneered by Ono Pharmaceutical Co., Ltd. in Japan. The drug was launched in Japan in 1995, and then registered in Europe and the United States in 1996. It is mainly used as an anti- Asthma and antiallergic drugs are effective drugs for the treatment of asthma. Its chemical structure is as follows: [0003] [0004] Due to its high efficiency, low toxicity, wide left and right range, few adverse reactions and many other advantages, it has quickly occupied the anti-asthma drug market since its launch and has become the focus of most attention in the international market. It has a very broad market potential. market expectation. Among them, 3-amino-2-hydroxyacetophenone is a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C221/00C07C225/22B01J19/00
CPCB01J19/0093B01J2219/0081B01J2219/00819B01J2219/00867B01J2219/00869C07C201/08C07C221/00C07C205/45C07C225/22
Inventor 任吉秋杨昆李海涛
Owner HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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