Methanol → 1-(4-Acetylphenyl)-1H-pyrrole-2,5-dione

HRID 652209Notes

Reaction equation

HRID 652209 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1.CO>CC(N(C)C)=O>[C:4]1(=[O:6])[N:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[C:1](=[O:7])[CH:2]=[CH:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 7468p-AminoacetophenoneHCID 7923Maleic Anhydride

Product 1

HCID 706601-(4-Acetylphenyl)-1H-pyrrole-2,5-dioneYield 65%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In dimethylacetamide, 98 g of maleic anhydride was reacted with 135 g of p-aminoacetophenone at 140° C. for 4 hours. After the reaction, methyl alcohol was added to the reaction solution to precipitate a solid. The precipitate was recovered by filtration and dried in vacuo to obtain 139 g (a yield of 65%) of p-maleimidoacetophenone.

Workup

  1. additionwas added to the reaction solution
  2. customto precipitate a solid
  3. filtrationThe precipitate was recovered by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-95ba40b84c154fadad6e98f96169379c
Source dataset
uspto-grants-1987_06
Patent number
US04670536

Reaction notes

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