1-Hexyl-4-methyl-3-nitro-5-methoxycarbonyl-2-pyridone → 3-Amino-1-hexyl-4-methyl-5-methoxycarbonyl-2-pyridone

HRID 1387285Notes

Reaction equation

HRID 1387285 reaction equation
[CH2:1]([N:7]1[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[C:10]([CH3:17])=[C:9]([N+:18]([O-])=O)[C:8]1=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C(OCC)(=O)C.[Pd]>[NH2:18][C:9]1[C:8](=[O:21])[N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[C:10]=1[CH3:17]

Participants

4

Reactant 1

HCID 217065051-Hexyl-4-methyl-3-nitro-5-methoxycarbonyl-2-pyridone

Product 1

HCID 217065343-Amino-1-hexyl-4-methyl-5-methoxycarbonyl-2-pyridoneYield 101.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-hexyl-4-methyl-3-nitro-5-methoxycarbonyl-2-pyridone (0.145 g, 0.49 mmol) and a catalytic amount of 10% Pd/C in ethyl acetate (100 mL) was hydrogenated at 45 psi in a Parr apparatus for 5 hours. The catalyst was removed by filtration and the solvent was evaporated to give 3-amino-1-hexyl-4-methyl-5-methoxycarbonyl-2-pyridone (0.133 g, 100%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-428d4e590fca4395ae3b97f8a5835bc2
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Reaction notes

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