4-Nitropyridine-2-carboxylic acid 1-oxide → 4-Aminopicolinic acid

HRID 1757257Notes

Reaction equation

HRID 1757257 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][N+:5]=1[O-])([OH:3])=[O:2]>C(O)(=O)C.[Pd]>[C:1]([C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][N:5]=1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 847134-Nitropyridine-2-carboxylic acid 1-oxide

Product 1

HCID 20501324-Aminopicolinic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-carboxy-4-nitropyridine N-oxide (0.5 g, 27 mmol) (E. Prafft et al., J. Prakt. Chem. 1961, 13, 58) in acetic acid (20 ml) was hydrogenated under pressure (70 psi) in the presence of Pd/C. (10%) (0.25 g) at ambient temperature for 2 hours. The catalyst was removed by filtration, and the filtrate evaporated to give 2-carboxy-4-aminopyridine as an off-white solid which was dried in a dessicator (300 mg, 80%).

Workup

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

Sources & evidence

ORD record
ord-23239d1e19a64d37a243bf24ea2648d3
Source dataset
uspto-grants-1995_08
Patent number
US05444057

Reaction notes

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