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

HRID 2202914Notes

Reaction equation

HRID 2202914 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

Reactant 1

HCID 896911684-(4-Chlorobenzyloxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1h)-one

Product 1

HCID 896902584-(4-Chlorobenzyloxy)-1-(4-amino-3-(methylamino)phenyl)pyridin-2(1h)-oneYield 49.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

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.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customwas neutralized with saturated NaHCO3 at 0° C.
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by NH silica gel column chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-1b2778efc9dd42cda5960c86b6c6622c
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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