Synthesis method of 3-amino-2-hydroxyacetophenone

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

Active Publication Date: 2018-02-16
HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology describes a new way to make certain chemicals called aminobicyclo[oxane (ABO) with specific structures like its molecule's core shell. These special features allow efficient mixing between different substances while minimizing any unwanted side products such as water vapor. Additionally, these processes have enhanced productivity rates compared to existing methods. Overall, this innovative technique allows for effective manufacture of various compounds from raw material overcomes their limitations.

Problems solved by technology

This patented technical problem addressed in the patents relates to improving the manufacturing methods for compounds called prerenilate analogues (PGRAs) such as PrENZOA®, while also addressing their challenges during commercial use due to these properties mentioned earlier.

Method used

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  • Synthesis method of 3-amino-2-hydroxyacetophenone
  • Synthesis method of 3-amino-2-hydroxyacetophenone
  • Synthesis method of 3-amino-2-hydroxyacetophenone

Examples

Experimental program
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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

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Claims

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Application Information

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Owner HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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