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Synthetic method of 3-aminophthalic anhydride

A synthesis method and technology of aminophthalic anhydride, applied in the field of synthesis of 3-aminophthalic anhydride, can solve problems such as pressurization, unfavorable industrialized production, etc., and achieve the effects of not easy to catch fire, good industrial application prospect, and avoiding dangerous operation.

Inactive Publication Date: 2014-02-19
SHANGHAI NEW HUALIAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the defect that the synthesis of 3-aminophthalic anhydride needs to be pressurized and unfavorable for industrialized production in the prior art, the inventor of the present application has established a kind of 3-nitrophthalic anhydride as raw material, which is catalyzed by feeding hydrogen under normal pressure. A synthetic method for obtaining 3-aminophthalic anhydride through hydrogenation reduction, which is beneficial to industrial production

Method used

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  • Synthetic method of 3-aminophthalic anhydride
  • Synthetic method of 3-aminophthalic anhydride

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Put 200g (1.04mol) of 3-nitrophthalic anhydride into a 5L three-necked flask, add 3L of ethyl acetate (EA), 20g (0.167mol) of anhydrous magnesium sulfate and 2g of dry 10% palladium carbon, and continue to pass through the Inject hydrogen, ensure that the bottle stopper is not pushed, keep the internal pressure slightly less than or equal to 1 standard atmospheric pressure, and stir and react at 20°C for 12 hours. Use TLC to track the reaction until it is complete (developing agent is n-hexane: ethyl acetate = 1:2), filter, then wash the filter cake with ethyl acetate, recover palladium carbon, concentrate the filtrate under reduced pressure to recover ethyl acetate, and precipitate the solid for After washing with ethanol, 140 g of white solid 3-aminophthalic anhydride was obtained, the content was 99%, and the yield was 82.5%. The structure of the product was confirmed by NMR. 1 H-NMR (CDCl 3 ,400MHz) the result is: 6.27 (2H), 7.1-7.8 (3H).

Embodiment 2

[0025] Put 200g (1.04mol) of 3-nitrophthalic anhydride into a 5L three-necked bottle, add 3L of acetone, 20g (0.167mol) of anhydrous magnesium sulfate and 2g of dry 10% palladium carbon, and continuously feed hydrogen under airtight conditions to ensure that no Push the bottle stopper, keep the internal pressure slightly less than or equal to 1 standard atmospheric pressure, and stir and react at 25°C for 12 hours. Use TLC to track the reaction until it is complete (developing agent is n-hexane: ethyl acetate = 1:2), filter, then wash the filter cake with ethyl acetate, recover palladium carbon, concentrate the filtrate under reduced pressure to recover ethyl acetate, and precipitate the solid for After washing with ethanol, 140 g of white solid 3-aminophthalic anhydride was obtained, the content was 99%, and the yield was 82.5%. The structure of the product was confirmed by NMR. 1 H-NMR (CDCl 3 ,400MHz) the result is: 6.27 (2H), 7.1-7.8 (3H).

Embodiment 3

[0027] Put 200g (1.04mol) of 3-nitrophthalic anhydride into a 5L three-necked flask, add 3L of ethyl acetate (EA), 20g (0.167mol) of anhydrous magnesium sulfate and 2g of dry 10% palladium carbon, and continue to pass through the Inject hydrogen, ensure that the bottle stopper is not pushed, keep the internal pressure slightly less than or equal to 1 standard atmospheric pressure, and stir and react at 35°C for 8 hours. Use TLC to track the reaction until it is complete (developing agent is n-hexane: ethyl acetate = 1:2), filter, then wash the filter cake with ethyl acetate, recover palladium carbon, concentrate the filtrate under reduced pressure to recover ethyl acetate, and precipitate the solid for After washing with ethanol, 140 g of white solid 3-aminophthalic anhydride was obtained, the content was 99%, and the yield was 82.5%. The structure of the product was confirmed by NMR. 1 H-NMR (CDCl 3 ,400MHz) the result is: 6.27 (2H), 7.1-7.8 (3H).

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Abstract

The invention discloses a synthetic method of 3-aminophthalic anhydride. The method comprises the following steps: (a) dissolving 3-nitrophthalic anhydride in an organic solvent, adding a dehydrating agent and a catalyst, introducing hydrogen, maintaining at 1 atm and stirring; (b) after complete reaction, filtering or centrifuging, concentrating and the recovering the organic solvent, so as to obtain a product 3-aminophthalic anhydride. According to the invention, 3-nitrophthalic anhydride is used as a raw material, which is introduced with hydrogen under the normal pressure to carry out catalytic hydrogenation reduction, so as to obtain 3-aminophthalic anhydride. The method does not need extra pressurization, avoids the operation danger caused by the pressurization and does not cause fire; therefore, the method is safe and effective, and conducive to the realization of industrialization production.

Description

technical field [0001] The invention belongs to the field of organic synthesis chemistry, and in particular relates to a synthesis method of 3-aminophthalic anhydride. Background technique [0002] 3-aminophthalic anhydride belongs to pharmaceutical intermediates, and can be further prepared into luminol, 3-hydroxyphthalic anhydride and other pharmaceutical intermediates. In the prior art, 3-aminophthalic anhydride can be synthesized from 3-nitrophthalic anhydride. 3-Nitrophthalic anhydride can be obtained by using phthalic anhydride as raw material, first nitrating with mixed acid, and then dehydrating and closing acetic anhydride, and there are many industrial productions. 3-aminophthalic anhydride has a wide source of raw materials, but there is no large-scale production of 3-aminophthalic anhydride at present. The existing retrieved literature uses 3-nitrophthalic anhydride as raw material, under the catalysis of nickel aluminum alloy, pressurizes hydrogen in acetone a...

Claims

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Application Information

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IPC IPC(8): C07D307/89
CPCC07D307/89
Inventor 李晓龙田旭彪柏挺张晓弟吴庆安周福群周秋火
Owner SHANGHAI NEW HUALIAN PHARMA