3-Methoxy-4-nitro-1-oxo-1lambda~5~-pyridine → 3-Methoxy-4-aminopyridine

HRID 266914Notes

Reaction equation

HRID 266914 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N+:5]([O-])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CO.[Ni]>[NH2:9][C:8]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 147627103-Methoxy-4-nitro-1-oxo-1lambda~5~-pyridine

Product 1

HCID 30167383-Methoxy-4-aminopyridine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-methoxy-4-nitropyridine-N-oxide (17.37 g, 0.102 mol) in MeOH (180 ml) was hydrogenated in a 500 ml Parr bottle at 40° C. and 40 psi for 3 hours using Raney Nickel as catalyst. After filtration of the catalyst and evaporation of the solvent, the residue was chromatographed on silica gel using CH2Cl2 /MeOH/NH4OH (90/10/1) as the eluent to give the title compound. The product was recrystallized from toluene to give 10.8 g (65%) of pure product, m.p. 94°-95° C. The structural assignment is supported by the proton NMR spectrum.

Workup

  1. customwas hydrogenated in a 500 ml Parr bottle at 40° C.
  2. filtrationAfter filtration of the catalyst and evaporation of the solvent
  3. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-7457f0086d1a48adbfe786d67aac15fe
Source dataset
uspto-grants-1997_07
Patent number
US05652363

Reaction notes

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