4-Aminobenzoic Acid → (Z)-4-(3-carboxyacrylamido)benzoic acid

HRID 1417353Notes

Reaction equation

HRID 1417353 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:17])[O:16][C:14](=[O:15])[CH:13]=[CH:12]1>CC(=O)C>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:11](=[O:17])/[CH:12]=[CH:13]\[C:14]([OH:16])=[O:15])=[CH:3][CH:4]=1)([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 7923Maleic Anhydride

Product 1

HCID 5717537(Z)-4-(3-carboxyacrylamido)benzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Aminobenzoic acid (17.24 g, 0.1257 mol) was added to a stirred solution of maleic anhydride (12.33 g, 0.1257 mol) in propanone (300 ml). Stirring was continued at room temperature for 3 hours. The product, which separated as a yellow solid, was collected by suction filtration and dried on the filter: mp 217°-219° C. (Ref: K C Liu, J. Chin. Chem. Soc., 1973, 20, 163).

Workup

  1. customThe product, which separated as a yellow solid
  2. filtrationwas collected by suction filtration
  3. customdried on the
  4. filtrationfilter

Sources & evidence

ORD record
ord-6a5a3a0446f54cc8ba981378399d2707
Source dataset
uspto-grants-1999_03
Patent number
US05877204

Reaction notes

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