2(1H)-Pyridinone, 5-ethyl-6-methyl-3-nitro- → 3-Amino-5-ethyl-6-methyl-1H-pyridin-2-one

HRID 1681109Notes

Reaction equation

HRID 1681109 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([N+:11]([O-])=O)[C:6](=[O:10])[NH:7][C:8]=1[CH3:9])[CH3:2].[H][H]>CO.O1CCCC1.[Pd]>[NH2:11][C:5]1[C:6](=[O:10])[NH:7][C:8]([CH3:9])=[C:3]([CH2:1][CH3:2])[CH:4]=1

Participants

6

Reactant 2

HCID 103523142(1H)-Pyridinone, 5-ethyl-6-methyl-3-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 4810223-Amino-5-ethyl-6-methyl-1H-pyridin-2-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A yellow solution of the 5-ethyl-6-methyl-3-nitro-2(1H)-pyridinone (10 g, 55 mmol) in a mixture of methanol and tetrahydrofuran (100 mL, 1:1 v/v) was reduced catalytically in the presence of 7% palladium on charcoal (0.7g) under and atmosphere of hydrogen (50 psi) at room temperature over a period of 3.5 hours. The resultant mixture was filtered through a small pad of Celite. The filtrate was concentrated under reduced pressure (15 torr) to provide the corresponding aminopyridone.

Workup

  1. customat room temperature
  2. customof 3.5 hours
  3. filtrationThe resultant mixture was filtered through a small pad of Celite
  4. concentrationThe filtrate was concentrated under reduced pressure (15 torr)

Sources & evidence

ORD record
ord-be932bcea0ab420d879e0a230894e848
Source dataset
uspto-grants-1992_12
Patent number
US05169769

Reaction notes

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