5-nitro-1-phenyl-1H-pyridin-2-one → 5-Amino-1-phenyl-1,2-dihydropyridin-2-one

HRID 2375893Notes

Reaction equation

HRID 2375893 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:16])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-])=O>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7](=[O:16])[N:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:9]=1

Participants

5

Reactant 1

HCID 223189695-nitro-1-phenyl-1H-pyridin-2-one

Product 1

HCID 587098035-Amino-1-phenyl-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-nitro-1-phenyl-1H-pyridin-2-one (60 mg, 0.28 mmol) in ethyl acetate (2 mL) and ethanol (2 mL) was added 5% Pd—C (10 mg), the resulting mixture was stirred under hydrogen atmosphere for 3 h. The catalyst was removed by filtration, and the filtrate was concentrated to give the title compound as a green oil. The product was used to next step without further purification. LC-MS (ES, Pos.): 187 [MH+], and 1H NMR (CDCl3, 400 MHz): δ=3.09 (br s, 2H), 6.60 (d, J=9.6 Hz, 1H), 6.82 (d, J=3.0 Hz, 1H), 7.12 (dd, J=9.6, 3.0 Hz, 1H), 7.37-7.41 (m, 3H), 7.45-7.49 (m, 2H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-efe36920eb734a8ea467ca59dd3d4388
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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