4-Aminobenzoic Acid → HCID 2859933, compound
Reaction equation
C([O-])([O-])=O.[K+].[K+].[NH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1.[CH:17]12[CH2:24][CH2:23][CH:20]([CH:21]=[CH:22]1)[CH:19]1[C:25]([O:27][C:28](=O)[CH:18]21)=[O:26]>O>[C:12]([C:11]1[CH:15]=[CH:16][C:8]([N:7]2[C:25](=[O:26])[CH:19]3[CH:18]([CH:17]4[CH2:24][CH2:23][CH:20]3[CH:21]=[CH:22]4)[C:28]2=[O:27])=[CH:9][CH:10]=1)([OH:14])=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of K2CO3 (5.88 g, 42.5 mmol) in H2O (100 mL) was added 4-aminobenzoic acid (5.83 g, 42.5 mmol) and bicyclo[2.2.2]oct-5-en-2,3-dicarboxylic anhydride (7.20 g, 40.4 mmol). The reaction mixture was stirred at room temperature for 18 hrs. and then washed with ethylacetate (EtOAc) (75 ml,). The aqueous phase was acidified with conc. HCl until the pH reached 1. The precipitated crystals were filtered and dried: 11.77 g (98%), mp=269° C.