4-Nitropyridine-2-carboxylic acid 1-oxide → 4-Aminopicolinic acid
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
Product 1
Reagents, catalysts & solvents 2
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
- customThe catalyst was removed by filtration
- customthe filtrate evaporated
Sources & evidence
- ORD record
- ord-23239d1e19a64d37a243bf24ea2648d3
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05444057
Reaction notes
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