Methyl 4-nitropyridine-2-carboxylate → Methyl 4-aminopyridine-2-carboxylate

HRID 488454

Reaction equation

HRID 488454 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:5]=1

Participants

4

Reactant 1

HCID 3352523Methyl 4-nitropyridine-2-carboxylate

Product 1

HCID 3759117Methyl 4-aminopyridine-2-carboxylateYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 4-nitropyridin-2-ylcarboxylate (0.7 g) (Deady et. al., Aus. J. Chem. 24 (1971)385-390) in methanol (30 ml) was treated with 10% Pd/C (0.3 g) and stirred under hydrogen at atmospheric pressure overnight. The solution was filtered and evaporated to yield the title compound (0.55 g). NMR δ(CDCl3) 3.97(3H,s), 4.34(2H, broad), 6.65(1H,dd), 7.39(1H,d), 8.32(1H,d).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-7f1060c725a74a8e9560e611ae4b9716
Source dataset
uspto-grants-2005_12
Patent number
US06972297B2

Linked notes

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