4-(4-Chlorobenzyloxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1h)-one → 4-(4-Chlorobenzyloxy)-1-(4-amino-3-(methylamino)phenyl)pyridin-2(1h)-one
Reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([NH:23][CH3:24])[CH:15]=3)[C:10](=[O:25])[CH:9]=2)=[CH:4][CH:3]=1>CC(O)=O.[Zn]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]3[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:9][C:10]2=[O:25])=[CH:15][C:16]=1[NH:23][CH3:24]Participants
4
Procedure
Zinc (20.34 g) was added to a suspension of 4-((4-chlorobenzyl)oxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1H)-one (12 g) in AcOH (200 ml) at room temperature. The mixture was stirred at room temperature for 1 h. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo. The residue was neutralized with saturated NaHCO3 at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (MeOH/EtOAc) to give the title compound (5.5 g) as a pale orange solid.