Dichloromethane → 4-(3-(1,3-Dioxolan-2-yl)-4-nitrophenyl)morpholine
Reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:7]=1.ClCCl.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:6]1[CH:7]=[C:2]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:3]=[CH:4][C:5]=1[N+:13]([O-:15])=[O:14]Participants
4
Procedure
2-(5-Chloro-2-nitrophenyl)-1,3-dioxolane (13.4 g, 58.4 mmol) was dissolved in morpholine (150 mL). The mixture was then heated to reflux for 16 hours. Cooling to room temperature, dichloromethane was added. The organic phase was washed with water, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product 4-(3-(1,3-dioxolan-2-yl)-4-nitrophenyl)morpholine (15.9 g, yield 97.1%).