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

HRID 224232

Reaction equation

HRID 224232 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[C:9]1(=O)[O:14][C:12](=[O:13])[CH:11]=[CH:10]1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CN(C)C=O>O>[OH:8][C:3]1[CH:4]=[CH:5][C:6]([N:7]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]2=[O:14])=[CH:1][CH:2]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 6228DimethylformamideHCID 7923Maleic AnhydrideHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 817341-(4-hydroxyphenyl)-1H-pyrrole-2,5-dioneYield 48.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

In a reactor, 30.0 g (0.275 moles) of p-aminophenol, 29.7 g (0.303 moles) of maleic anhydride, 39.0 g (0.275 moles) of phosphorus pentoxide and 100 g of dimethylformamide were charged and stirred at 15° C. for 2 hours. The reaction mixture was then gradually heated to 60° C., at which temperature the reaction was further continued for 2.5 hours. After cooling to room temperature, the resulting reaction mixture was admixed with water to precipitate N-(p-hydroxyphenyl) maleimide in the form of crystals. The crystals were separated by filtration, washed with water and then dried to obtain 25.1 g (0.133 moles) of N-(p-hydroxyphenyl) maleimide (yield 48.2%).

Workup

  1. temperatureThe reaction mixture was then gradually heated to 60° C., at which temperature the reaction
  2. waitwas further continued for 2.5 hours
  3. temperatureAfter cooling to room temperature
  4. customthe resulting reaction mixture
  5. customto precipitate N-(p-hydroxyphenyl) maleimide in the form of crystals
  6. customThe crystals were separated by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-0c376d98037b459695cb4da196558734
Source dataset
uspto-grants-1980_11
Patent number
US04231934

Linked notes

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