HCID 89690578, compound → HCID 89690567, compound

HRID 2202970Notes

Reaction equation

HRID 2202970 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([NH:24][CH3:25])[CH:16]=2)[C:11](=[O:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.[Zn]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([N:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]2=[O:26])=[CH:16][C:17]=1[NH:24][CH3:25]

Participants

4

Reactant 1

HCID 89690578HCID 89690578, compound

Product 1

HCID 89690567HCID 89690567, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc (9.49 g) was added to a solution of 4-(benzyloxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1H)-one (5.1 g) in AcOH (120 ml) at room temperature. The mixture was stirred at room temperature for 2 h. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo. The mixture was neutralized with saturated NaHCO3 solution 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 washed with IPE and dried to give the title compound (3.5 g) as a brown solid.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customwas neutralized with saturated NaHCO3 solution 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. washThe residue was washed with IPE
  10. customdried

Sources & evidence

ORD record
ord-42171907ad0648b0bf53caa001a09ca4
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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