Benzene → HCID 178420620, compound
Reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C([CH:15](C([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24]C=1)=O)[C:16]([OH:18])=[O:17])(O)=O.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[OH2:34].[CH:35]1[CH:40]=CC=CC=1>>[OH:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[CH:40][C:35]([NH:28][C:33]2[C:15](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:16]([O-:18])=[O:17])=[O:34])=[CH:4][C:5]=1[O:6][CH3:7].[NH2+:21]1[CH2:22][CH2:27][CH2:26][CH2:25][CH2:24]1Participants
6
Procedure
A solution of 2.54 g of vanillin, 3.8 g of 2-carboxymalonanilic acid, and 1.43 g of piperidine in 20 ml of benzene is heated for 3 hours under reflux with removal of water of reaction. After completion of the reaction, the reaction mixture is cooled and the precipitated crystals are collected by filtration and dried to obtain 6.3 g of piperidinium N-(4-hydroxy-3-methoxycinnamoyl)anthranilate (94.7% yield), m.p. 188°-189° C. The compound structure is confirmed by elemental analysis, and by IR and NMR spectroscopy.