4-Aminobenzoic Acid → HCID 2341965, compound

HRID 1441199Notes

Reaction equation

HRID 1441199 reaction equation
[CH3:1][C:2]1=[C:3]([CH3:9])[C:4]([O:6][C:7]1=[O:8])=O.[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>CC(C)=O>[C:15]([C:14]1[CH:18]=[CH:19][C:11]([N:10]2[C:4](=[O:6])[C:3]([CH3:9])=[C:2]([CH3:1])[C:7]2=[O:8])=[CH:12][CH:13]=1)([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 7918Acetic AnhydrideHCID 13010Dimethylmaleic anhydrideHCID 517045Sodium Acetate

Product 1

HCID 2341965HCID 2341965, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

37.8 g (0.3 mol) of dimethylmaleic anhydride was slowly added to a solution of 41.1 g (0.3 mol) of p-aminobenzoic acid and 300 ml of acetone in a 250 ml flask at 10° C. The mixture was stirred for 2 hours to obtain a yellow precipitate. Thereafter, the precipitate was collected by filtration under reduced pressure and recrystallized from a solution of DMF/water (50:50 (w/w)) to give an intermediate. The intermediate was treated with sodium acetate and acetic anhydride at 85° C. for 4 hours, cooled to room temperature, and placed in an ice bath to obtain a precipitate. The precipitate was collected by filtration under reduced pressure and recrystallized from a solution of ethanol/water (50:50 (w/w)) to give N-(p-carboxyphenyl)dimethylmaleimide.

Workup

  1. customto obtain a yellow precipitate
  2. filtrationThereafter, the precipitate was collected by filtration under reduced pressure
  3. customrecrystallized from a solution of DMF/water (50:50 (w/w))
  4. customto give an intermediate
  5. customplaced in an ice bath
  6. customto obtain a precipitate
  7. filtrationThe precipitate was collected by filtration under reduced pressure
  8. customrecrystallized from a solution of ethanol/water (50:50 (w/w))

Sources & evidence

ORD record
ord-e1876de077cb4ea28762bb59d8f524d0
Source dataset
uspto-grants-2010_02
Patent number
US07655155B2

Reaction notes

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