Piperidine → 3-(2-Furoyl)-2-methylquinoline

Reaction equation

[C:1]1(C)[CH:6]=C[C:4]([NH:7][C:8]2C=CC=C[C:9]=2C=O)=[CH:3][CH:2]=1.[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([CH2:24][C:25](=O)[CH3:26])=[O:23].N1CCCCC1>C(O)C>[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([C:24]1[C:8]([CH3:9])=[N:7][C:4]2[C:26]([CH:25]=1)=[CH:6][CH:1]=[CH:2][CH:3]=2)=[O:23]

Participants

Procedure

A solution of 410 mg (1.95 mmol) N-(p-tolyl)-o-aminobenzaldehyde 326 mg (2.15 mmol), (2-furoyl)acetone and 50 mg piperidine in 4 ml 95% ethanol was heated overnight under reflux. Removal of he volatile materials left a black, gummy oil which was taken up in dichloromethane and, after being washed with 3M NaOH, brine, and dried (MgSO4), purified by flash chromatography [eluent, 3:2 pentane-diethyl ether (3:2)] yielding 355 mg (1.50 mmol, 77%) product.