Benzene → HCID 178420620, compound

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].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:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[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:3]=1[O:10][CH3:11].[NH2+:21]1[CH2:22][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Reactant 5

HCID 20222317HCID 20222317, compound

Product 1

HCID 178420620HCID 178420620, compound

Procedure

A solution of 2.54 g of 4-hydroxy-3-methoxybenzaldehyde, 3.8 g of 2-carboxymalonanilic acid, and 4.29 g of piperidine in 17 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 6.34 g of piperidinium N-(4-hydroxy-3-methoxycinnamoyl)anthranilate, mp. 188°-189° C. The compound structure is confirmed by elemental analysis, and by IR and NMR spectroscopy.