Hydrochloric Acid → 4-Propionamidocinnamic acid

Reaction equation

[C:1]([NH:5][C:6]1[CH:18]=[CH:17][C:9]([CH:10]=[CH:11][C:12]([O:14]CC)=[O:13])=[CH:8][CH:7]=1)(=[O:4])[CH2:2][CH3:3].[OH-].[Na+].Cl>C(O)C>[C:1]([NH:5][C:6]1[CH:18]=[CH:17][C:9]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[CH:8][CH:7]=1)(=[O:4])[CH2:2][CH3:3]

Participants

Procedure

To a solution of ethyl 4-propionamidocinnamate (160 mg) in ethanol (5 ml) was added 1N aqueous sodium hydroxide solution (1.5 ml) at ambient temperature. The mixture was stirred at same temperature for 14 hours, and then at 40° C. for 2 hours. 1N-hydrochloric acid (1.5 ml) was added to the reaction mixture and evaporated in vacuo. The residue was diluted with 10% methanol-dichloromethane, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from diisopropyl ether to give 4-propionamidocinnamic acid (115 mg) as a colorless powder. mp: 243° C.