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

HRID 424297Notes

Reaction equation

HRID 424297 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.[Na+].C(OC(=O)C)(=O)C>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

6

Reactant 4

HCID 9784-Aminobenzoic Acid2×HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 517045Sodium Acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

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

Workup

  1. customat 10° C. to obtain a yellow precipitate
  2. customThis precipitate was recrystallized with a solution of DMF (dimethylformamide) and ethanol (50:50, w/w)
  3. customto form an intermediate
  4. additionThe intermediate was treated at 85° C. for 15 minutes
  5. customwas then precipitated in an ice water bath
  6. customto obtain a precipitate
  7. customThe obtained precipitate was recrystallized with a solution of ethyl acetate and n-hexane (50:50, w/w)

Sources & evidence

ORD record
ord-efed8329339448f6817e422c97933580
Source dataset
uspto-grants-2012_01
Patent number
US08105663B2

Reaction notes

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