1-methyl-5-nitro-2(1H)-pyridinone → 5-Amino-1-methyl-1,2-dihydropyridin-2-one

HRID 2375866Notes

Reaction equation

HRID 2375866 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:11])[N:8]([CH3:10])[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:11])[N:8]([CH3:10])[CH:9]=1

Participants

5

Reactant 1

HCID 2958661-methyl-5-nitro-2(1H)-pyridinone

Product 1

HCID 102200055-Amino-1-methyl-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-nitro-1-methyl-2(1H)-pyridone (154 mg, 0.999 mmol) in ethyl acetate (3 mL) and ethanol (3 mL) was added 5% Pd—C (36 mg), and the resulting mixture was stirred under hydrogen atmosphere overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo to obtain the title compound as light-green oil. 1H NMR (CD3OD 400 MHz): δ=3.53 (s, 3H), 6.49 (d, 1H, J=9.6 Hz), 7.07 (d, 1H, J=3.2 Hz), 7.28 (dd, 1H, J=2.8 & 9.6 Hz). MS (ES+): m/z 125.04 (100) [MH+]. HPLC: tR=0.43 min (ZQ2000, polar—5 min).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b2a5737b7d4b43518a64b7520ff4308f
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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