4-Nitroaniline → 1,4-Dimethyl 2-[(4-nitrophenyl)amino]but-2-enedioate

HRID 1070472Notes

Reaction equation

HRID 1070472 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]([C:17]([O:19][CH3:20])=[O:18])#[C:12][C:13]([O:15][CH3:16])=[O:14]>CO>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:12](=[CH:11][C:17]([O:19][CH3:20])=[O:18])[C:13]([O:15][CH3:16])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 6052251,4-Dimethyl 2-[(4-nitrophenyl)amino]but-2-enedioateYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-nitroaniline (6.91 g, 50 mmol) and dimethyl acetylenedicarboxylate (7.82 g, 55 mmol) in methanol (100 ml) was refluxed under heating for 24.5 hr. The reaction vessel was cooled to room temperature and allowed to stand for a day. The resulting crystals were collected by filtration to give dimethyl 2-[(4-nitrophenyl)amino]-2-butenedioate (6.43 g, 46%, yellow crystals).

Workup

  1. temperatureunder heating for 24.5 hr
  2. waitto stand for a day
  3. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-29b521eadabb49f787fbe381a897ee2d
Source dataset
uspto-grants-2005_06
Patent number
US06903094B2

Reaction notes

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