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Synthetic process for diacerein

A synthesis process and a technology for diacerein are applied in the new synthesis process field of high-purity diacerein, and can solve the problems of high aloe-emodin residue, high cost, unfavorable industrialization, low product yield and purity, etc. Avoid the use of chromium-containing oxidants, the process is easy to control, and the product is easy to achieve

Inactive Publication Date: 2012-12-19
SHANGHAI HUATUO MEDICAL SCI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this process avoids the use of chromium oxidant, its process reaction route is long, new impurities and reagents are introduced in the reaction, and the yield and purity of the obtained product are low, and it needs to be further refined before it can be used, so the high cost is not conducive to industrialization
Patent WO2006051400A1 (2006) reports that aloe-emodin can be directly oxidized to rhein with a sodium nitrite-concentrated sulfuric acid oxidation system. The reagent cost of this method is relatively low, but the obtained rhein has a low purity. The residue is high, and at the same time, due to the use of concentrated sulfuric acid as a solvent, a large amount of waste acid water needs to be treated after the reaction

Method used

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  • Synthetic process for diacerein
  • Synthetic process for diacerein

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Suspend aloe-emodin (100g) in N,N-dimethylformamide (1000mL), add sodium tungstate (1g), heat to about 80°C to completely dissolve aloe-emodin, and add to the reaction solution Slowly add 30wt% hydrogen peroxide (500mL) dropwise in the medium, and keep the reaction temperature at about 100°C until the hydrogen peroxide is added dropwise, and solids will gradually precipitate out. TLC or HPLC will track until the reaction is completely transformed. Starch potassium iodide reagent detects that there is no peroxide in the reaction system. The residue was cooled to room temperature, the precipitated solid was filtered, washed with water, and dried to obtain 101 g of rhein. The HPLC purity was 98.8%, and the yield was 96.2%.

Embodiment 2

[0030] Suspend aloe-emodin (100g) in N,N-dimethylformamide (300mL), add sodium tungstate (0.5g), heat to reflux to completely dissolve aloe-emodin, and slowly add to the reaction solution Add dropwise 30wt% hydrogen peroxide (200mL), maintain the reaction reflux, until the hydrogen peroxide is added dropwise, gradually solids are precipitated, TLC or HPLC is followed until the reaction conversion is complete, starch potassium iodide reagent detects that there is no peroxide residue in the reaction system, cool to room temperature, The precipitated solid was filtered, washed with water, and dried to obtain 101 g of rhein, with an HPLC purity of 98.5% and a yield of 96.2%.

Embodiment 3

[0032] Suspend aloe-emodin (100g) in N,N-dimethylacetamide (1000mL), add sodium tungstate (2g), heat to about 80°C to completely dissolve aloe-emodin, and add to the reaction solution Slowly add 30wt% hydrogen peroxide (500mL) dropwise in the medium, and keep the reaction temperature at about 100°C until the hydrogen peroxide is added dropwise, and solids will gradually precipitate out. TLC or HPLC will track until the reaction is completely transformed. Starch potassium iodide reagent detects that there is no peroxide in the reaction system. , cooled to room temperature, filtered the precipitated solid, washed with water, and dried to obtain 100 g of rhein, the HPLC purity was 98.9%, and the yield was 95.2%.

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Abstract

The invention discloses a synthetic process for diacerein. The process comprises the steps of oxidizing aloe-emodin to produce chrysophanic acid under double combination effects of a catalyst and hydrogen peroxide, keeping a temperature of 80 DEG C to the refluxing temperature of a solvent, and reacting for 1-5 hours; and performing an acetylation reaction on the chrysophanic acid to form the diacerein. In the process, a chromium-containing oxidant used by a conventional process is avoided; an inexpensive and easily available, environment-friendly and mild-reaction oxidant is employed; the process is easy to control; and the obtained product quality is greatly improved, so that the process is particularly suitable for industrialized large-scale production.

Description

technical field [0001] The invention relates to a new synthesis process of diacerein, an active ingredient of medicine for treating arthritis, in particular to a new synthesis process of high-purity diacerein. Background technique [0002] Diacerein, the chemical name is 4,5-diacetyl-9,10-dihydro-9,10-dioxo-2-anthracene carboxylic acid, which is the diacetylation product of phenolic hydroxyl group of rhein, as an interleukin The inhibitor of IL-1β is clinically used for the treatment of degenerative arthritis. [0003] The synthesis of diacerein has been reported in many literatures. The main synthesis method is to use aloin as raw material, obtain aloe-emodin through deglycoside, and then oxidize aloe-emodin to rhein and then carry out acetylation reaction to synthesize it. The oxidation of aloe-emodin is a key step. The earliest patent DE2711493A1 (1977) reported that using potassium dichromate as an oxidant can directly oxidize the alcoholic hydroxyl group of aloe-emodi...

Claims

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Application Information

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IPC IPC(8): C07C69/16C07C67/08
Inventor 黄金文施小风单园园朱勤
Owner SHANGHAI HUATUO MEDICAL SCI CO LTD
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