4-Aminophenol → 1-(4-hydroxyphenyl)-1H-pyrrole-2,5-dione

HRID 2057048Notes

Reaction equation

HRID 2057048 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]1(=O)[O:14][C:12](=[O:13])[CH:11]=[CH:10]1>C(O)(=O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]2=[O:14])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 7923Maleic Anhydride

Product 1

HCID 817341-(4-hydroxyphenyl)-1H-pyrrole-2,5-dioneYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The suspension that consists of 5.0 g (45.8 mmol) of 4-aminophenol, 4.49 g of maleic acid anhydride and 40 ml of acetic acid is refluxed for 3 hours. It is concentrated by evaporation, residual acetic acid is removed azeotropically by repeated distillation with acetic acid, and the residue is purified by chromatography on fine silica gel. 2.83 g (15.0 mmol, 33%) of the title compound is isolated.

Workup

  1. temperatureis refluxed for 3 hours
  2. concentrationIt is concentrated by evaporation, residual acetic acid
  3. customis removed azeotropically
  4. distillationdistillation with acetic acid
  5. customthe residue is purified by chromatography on fine silica gel

Sources & evidence

ORD record
ord-6c106bbe72ad4d04be8301c245ccc8d8
Source dataset
uspto-grants-2008_02
Patent number
US07335775B2

Reaction notes

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