4-((4-Fluorobenzyl)oxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1H)-one → 1-(4-Amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one
Reaction equation
[F: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]([F: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
To a suspension of 4-((4-fluorobenzyl)oxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1H)-one (500 mg) in AcOH (30 ml) was added zinc (885 mg), and the mixture was stirred at room temperature for 1 h. The insoluble material was removed by filtration and washed with MeOH. The filtrate was concentrated, and partitioned between EtOAc, THF and saturated NaHCO3 solution. The organic layer was then washed with brine, dried over MgSO4, and concentrated. The resulting solid was collected, and washed with IPE to give the title compound (366 mg) as a brown solid.
Workup
- customThe insoluble material was removed by filtration
- washwashed with MeOH
- concentrationThe filtrate was concentrated
- custompartitioned between EtOAc, THF and saturated NaHCO3 solution
- washThe organic layer was then washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe resulting solid was collected
- washwashed with IPE
Sources & evidence
- ORD record
- ord-638e35d32034432eb819ab6ef355d695
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365540B2
Reaction notes
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