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Method for preparing dimethyl acetamidophthalate

A technology of dimethyl acetamidophthalate and nitrophthalic anhydride, which is applied in the field of organic synthesis, can solve problems such as low synthesis efficiency and lengthy steps, and achieves improved production efficiency and the formation of acetic acid p-acetamide. The effect of promotion

Active Publication Date: 2020-08-07
YANGZHOU POLYTECHNIC INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, it is mostly prepared by multi-step reactions such as nitrophthalic anhydride through nitro reduction, acid anhydride acidification, esterification, and acetylation. The steps are lengthy and the synthesis efficiency is low.

Method used

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  • Method for preparing dimethyl acetamidophthalate
  • Method for preparing dimethyl acetamidophthalate
  • Method for preparing dimethyl acetamidophthalate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] (1) Put urea (50g) in an alumina crucible and put it into a muffle furnace, heat it up to 550°C at a heating rate of 5°C / min, keep it warm for 5h, and then cool it down to room temperature naturally, then place it in a dilute nitric acid solution (0.1 mol / L, 200mL) after stirring for 5min, the precipitate was filtered and dried at 80°C to obtain g-C 3 N 4 ;

[0017] (2) Dissolve copper acetate monohydrate (1mmol) in ethanol (50mL), heat up to 50°C, add glucose solution (0.2mol / L, 50mL) and sodium hydroxide solution (0.3mol / L, 50mL) and the g-C prepared in step (1) 3 N 4 (take 2.0g), after reacting for 15min, stop heating and stirring, after naturally cooling to room temperature, filter, precipitate is washed with deionized water, dry to obtain graphite phase carbon nitride supported cuprous catalyst (g-C 3 N 4 / Cu 2 O, hereinafter referred to as product A).

Embodiment 2

[0019] (1) Put urea (50g) in an alumina crucible and put it into a muffle furnace, heat it up to 600°C at a heating rate of 10°C / min, keep it warm for 3 hours, and then cool it down to room temperature naturally, then place it in a dilute nitric acid solution (0.2 mol / L, 200mL) after stirring for 10min, the precipitate was filtered and dried at 60°C to obtain g-C 3 N 4 ;

[0020] (2) Disperse copper sulfate pentahydrate (1mmol) in ethanol (100mL), heat up to 60°C, add glucose solution (0.1mol / L, 100mL) and sodium hydroxide solution (0.15mol / L, 100mL) under stirring ) and the g-C prepared in step (1) 3 N 4 (take 2.5g), after reacting for 10min, stop heating and stirring, after natural cooling to room temperature, filter, precipitate is washed with deionized water, dry to obtain graphite phase carbon nitride supported cuprous catalyst (g-C 3 N 4 / Cu 2 O, hereinafter referred to as product B).

Embodiment 3

[0022]

[0023] Weigh compound 1 (1mmol) and dissolve it in methanol (12mL), add 200mg of product A and acetic anhydride (2.0mmol) at room temperature, stir and react for 12 hours, filter, and after the filtrate is concentrated under reduced pressure, it is purified by silica gel column chromatography (EtOAc / petroleum ether=1 / 20 to 1 / 15) to obtain compound 2 (217mg, 86.4%), and the structural confirmation data of compound 2 are as follows:

[0024] Compound 2: m.p.104-105°C; ESIMS m / z 252.1[M+H] + ;Elemental AnalysisC 12 h 13 NO 5 : (theoretical value C, 57.37; H, 5.22, N, 5.58) measured value C, 57.60; H, 5.26; N, 5.65; 1 H NMR (400MHz, DMSO-d 6 )δ H 10.16(s,1H,N H Ac),7.82-7.65(m,2H,Ph-H),7.58-7.50(m,1H,Ph-H),3.80(s,3H,COOMe),3.78(s,3H,COOMe),2.21(s ,3H,COC H 3 ).

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Abstract

The invention relates to a method for preparing dimethyl acetamidophthalate. The method comprises the following steps: dissolving nitrophthalic anhydride in methanol, adding a graphite-phase carbon nitride supported cuprous catalyst (g-C3N4 / Cu2O) and acetic anhydride, and carrying out reacting to obtain dimethyl acetamidophthalate. 200-300 mg of the graphite-phase carbon nitride supported cuprouscatalyst (g-C3N4 / Cu2O) is used for every millimole of nitrophthalic anhydride, and 2.0-3.0 mmol of acetic anhydride is used for every millimole of nitrophthalic anhydride.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing dimethyl acetamidophthalate. Background technique [0002] The derivatives of dimethyl acetamidophthalate have important uses in the fields of medicine, chemical industry and dyestuff. In the prior art, nitrophthalic anhydride is mostly prepared by multi-step reactions such as nitro reduction, anhydride acidification, esterification, and acetylation. The steps are lengthy and the synthesis efficiency is low. A kind of graphitic phase carbon nitride supported cuprous catalyst (g-C 3 N 4 / Cu 2 O), it is jointly catalyzed with the acetic anhydride of catalytic amount, realized to prepare aminophthalic acid dimethyl ester by one step of nitrophthalic anhydride. In order to overcome the above-mentioned deficiencies in the prior art, the applicant adopts the above-mentioned g-C 3 N 4 / Cu 2 The O catalyst and the adjustment of the dosage of acet...

Claims

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Application Information

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IPC IPC(8): C07C229/62C07C227/12B01J27/24
CPCC07C227/12B01J27/24C07C229/62Y02P20/584
Inventor 岳金方雍达明罗志臣王雪源袁书婷侯海超
Owner YANGZHOU POLYTECHNIC INST
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