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

HRID 421525Notes

Reaction equation

HRID 421525 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]1(=O)[O:16][C:14](=[O:15])[CH:13]=[CH:12]1>C(O)(=O)C>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([N:1]2[C:14](=[O:15])[CH:13]=[CH:12][C:11]2=[O:16])=[CH:3][CH:4]=1)([OH:8])=[O:7]

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 176Acetic AcidSolvent

Procedure

41.1 g (0.3 mol) of p-aminobenzoic acid and 300 ME of acetic acid were put into a 250 Ml flask, dissolved, and then 29.4 g (0.3 mol) of maleic acid anhydride was slowly added at 10° C. to obtain a yellow precipitate. This yellow precipitate was recrystallized using a mixed solution of DMF and ethanol (50:50, w/w). The recrystallized intermediate was treated at 85° C. for 15 minutes using sodium acetate and acetic acid anhydride, cooled to room temperature, and then precipitated using an ice water bath to obtain a precipitate. The obtained precipitate was recrystallized using a mixed solution of ethyl acetate and n-hexane (50:50, w/w) to obtain N-(p-carboxyphenyl) maleimide.

Workup

  1. dissolutiondissolved
  2. customto obtain a yellow precipitate
  3. customThis yellow precipitate was recrystallized
  4. additionThe recrystallized intermediate was treated at 85° C. for 15 minutes
  5. customprecipitated
  6. customto obtain a precipitate
  7. customThe obtained precipitate was recrystallized

Sources & evidence

ORD record
ord-840988c77d274baa8fe6b29fd6104ad0
Source dataset
uspto-grants-2012_01
Patent number
US08101248B2

Reaction notes

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