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Chloramphenicol drug intermediate p-nitroacetophenone synthesis method

A technology of p-nitroacetophenone and its synthesis method, which is applied in the field of organic synthesis, can solve problems such as complex process and low yield, and achieve the effects of increasing reaction yield, shortening reaction time, and reducing intermediate links in the reaction

Inactive Publication Date: 2018-07-03
CHENGDU QIESITE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the existing synthetic methods use p-nitroethylbenzene as the reactant, the process is more complicated, and the yield is not high, so it is necessary to propose a new synthetic method

Method used

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  • Chloramphenicol drug intermediate p-nitroacetophenone synthesis method
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  • Chloramphenicol drug intermediate p-nitroacetophenone synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The synthetic method of chloramphenicol pharmaceutical intermediate p-nitroacetophenone, comprises the steps:

[0019] A. Add 3mol of 3-bromo-4-(1-hydroxyethyl)-nitrobenzene and 300ml of potassium bromide solution with a mass fraction of 10% into the reaction vessel, control the stirring speed at 160rpm, and add 4mol with a mass fraction of 55% 3-methylbutylamine solution, raise the temperature of the solution to 40°C, add 2mol of ammonium chlororhodate in 3 times, continue the reaction for 40min after the addition, and raise the temperature of the solution to 50°C;

[0020] B, adding mass fraction is 60% chlorinated isopentane solution to wash 3 times, mass fraction is 70% 4-chloro-1-butanol solution to wash 5 times, mass fraction is 30% potassium sulfate solution to wash 3 times , the solution is separated into layers, the oil layer is separated, the temperature is lowered to 10° C., recrystallized in a chlorodibutylene solution with a mass fraction of 90%, and dehydr...

Embodiment 2

[0022] The synthetic method of chloramphenicol pharmaceutical intermediate p-nitroacetophenone, comprises the steps:

[0023] A, 3-bromo-4-(1-hydroxyethyl)-nitrobenzene, 400ml mass fraction of 13% potassium bromide solution is added to the reaction vessel, the stirring speed is controlled at 170rpm, and 4.5mol mass fraction is added to be 60 % of 3-methylbutylamine solution, raise the solution temperature to 45°C, add 2.5mol ammonium chlororhodiumate in 5 times, continue to react for 50min after adding, raise the solution temperature to 53°C;

[0024] B, adding mass fraction is 62% chloroisopentane solution to wash 4 times, mass fraction is 73% 4-chloro-1-butanol solution to wash 6 times, mass fraction is 32% potassium sulfate solution to wash 5 times , the solution was separated into layers, the oil layer was separated, the temperature was lowered to 13° C., recrystallized in a chlorodibutylene solution with a mass fraction of 93%, and dehydrated with anhydrous calcium sulfat...

Embodiment 3

[0026] The synthetic method of chloramphenicol pharmaceutical intermediate p-nitroacetophenone, comprises the steps:

[0027] A. Add 3-mol of 3-bromo-4-(1-hydroxyethyl)-nitrobenzene and 500 ml of potassium bromide solution with a mass fraction of 16% into the reaction vessel, control the stirring speed at 190 rpm, and add 5 mol with a mass fraction of 63% 3-methylbutylamine solution, raise the temperature of the solution to 50°C, add ammonium chlororhodate in 5 times, continue the reaction for 60min after the addition, and raise the temperature of the solution to 57°C;

[0028] B, adding mass fraction is 65% chloroisopentane solution to wash 6 times, mass fraction is 77% 4-chloro-1-butanol solution to wash 7 times, mass fraction is 35% potassium sulfate solution to wash 6 times, The solution was separated into layers, the oil layer was separated, the temperature was lowered to 15° C., recrystallized in a chlorodibutylene solution with a mass fraction of 96%, and dehydrated wit...

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Abstract

The invention discloses a chloramphenicol drug intermediate p-nitroacetophenone synthesis method, which comprises: adding 3-bromo-4-(1-hydroxyethyl)-nitrobenzene and a potassium bromide solution intoa reaction container, stirring, adding a 3-methyl butylamine solution, increasing the temperature of the solution, adding ammonium hexachlororhodate, continuously carrying out the reaction after completing the adding, and increasing the temperature of the solution; and adding a chloroisopentane solution, washing multiple times, washing multiple times with a 4-chloro-1-butanol solution, washing multiple times with a potassium sulfate solution, layering the solution, extracting the oil layer, reducing the temperature, re-crystallizing in a chlorodibutene solution, and dehydrating with a dehydrating to obtain the finished product p-nitroacetophenone.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, belonging to the field of organic synthesis, in particular to a synthesis method of p-nitroacetophenone, a chloramphenicol pharmaceutical intermediate. Background technique [0002] p-Nitroacetophenone is mainly used as a pharmaceutical intermediate of chloramphenicol and a dye intermediate. Chloramphenicol antibiotics can act on the 50S subunit of bacterial ribonucleosomes to prevent protein synthesis, and are antibacterial broad-spectrum antibiotics. The 70S ribosome of bacterial cells is the main cellular component of protein synthesis, which includes two subunits of 50S and 30S. Chloramphenicol reversibly binds to the 50S subunit, blocks the action of transpeptidylase, and interferes with the combination of the aminoacyl-tRNA terminal with amino acids and the 50S subunit, thereby hindering the formation of new peptide chains and inhibiting protein synthesis. Because c...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/45
CPCC07C201/12C07C205/45
Inventor 彭飞
Owner CHENGDU QIESITE TECH CO LTD
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