4-Aminobenzoic Acid → 4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid

HRID 1614695Notes

Reaction equation

HRID 1614695 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1>CC(C)=O>[C:13]([C:12]1[CH:16]=[CH:17][C:9]([N:8]2[C:1](=[O:7])[CH:2]=[CH:3][C:4]2=[O:6])=[CH:10][CH:11]=1)([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 7923Maleic Anhydride

Product 1

HCID 869254-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(para-carboxyphenyl)maleimide was prepared as follows. Maleic anhydride (45.2 grams (g)) was dissolved in from 300-400 milliliters (ml) of acetone. To this solution, an equimolar amount of para-aminobenzoic acid (63.2 g) was added with rapid stirring. The reaction mixture solidified within a few seconds. Excess solvent was removed by evaporation to yield the amic acid intermediate which was then dried overnight at 65° C. under vacuum.

Workup

  1. waitThe reaction mixture solidified within a few seconds
  2. customExcess solvent was removed by evaporation

Sources & evidence

ORD record
ord-d93794e0c49b4dfcb0154889be6628ad
Source dataset
uspto-grants-1993_03
Patent number
US05198551

Reaction notes

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