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

HRID 1589784Notes

Reaction equation

HRID 1589784 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]>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

5

Reactant 1

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

Product 1

HCID 4810223-Amino-5-ethyl-6-methyl-1H-pyridin-2-oneYield 68.1%

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 (0.7 g) under an 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 5.7 g (68%) of the corresponding aminopyridone.

Workup

  1. filtrationThe resultant mixture was filtered through a small pad of Celite
  2. concentrationThe filtrate was concentrated under reduced pressure (15 torr)

Sources & evidence

ORD record
ord-6254c9a9232e465eb40715f9398499a4
Source dataset
uspto-grants-1993_04
Patent number
US05200329

Reaction notes

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