Nitrosobenzene → (E)-N-hydroxy-2-methyl-N,3-diphenylacrylamide

Reaction equation

C1CCN2C(=NCCC2)CC1.[CH3:12]/[C:13](=[CH:16]\[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)/[CH:14]=[O:15].[N:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24]>ClCCl>[OH:24][N:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:14](=[O:15])/[C:13](/[CH3:12])=[CH:16]/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Procedure

DBU (15 mg, 0.1 mmol) was added under argon to a solution of (E)-2-methyl-3-phenylacrylaldehyde (146 mg, 1 mmol), nitrosobenzene (107 mg, 1 mmol) and catalyst (36.4 mg, 0.1 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 10 min. The solvent was removed under vacuum, and the residue was purified by flash silica gel column chromatography using hexane and ethyl acetate as the eluents.