3-Nitro-2-vinylpyridine → 2-Ethylpyridin-3-amine

HRID 1784878Notes

Reaction equation

HRID 1784878 reaction equation
[N+:1]([C:4]1[C:5]([CH:10]=[CH2:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.C(OCC)(=O)C.[Pd]>[CH2:10]([C:5]1[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][N:6]=1)[CH3:11]

Participants

4

Reactant 1

HCID 118296173-Nitro-2-vinylpyridine

Product 1

HCID 218818002-Ethylpyridin-3-amineYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 0.220 g (1.47 mmol) of 3-nitro-2-vinyl-pyridine dissolved in 1:1 methanol/ethyl acetate was added 0.010 g of Pd/C. The resulting mixture was hydrogenated overnight at 50 psi. Filtration and removal of solvent provided 0.160 g (89% yield) of 2-ethyl-pyridin-3-ylamine.

Workup

  1. filtrationFiltration and removal of solvent

Sources & evidence

ORD record
ord-c6a65ec3dd0942a3b631b6ed572f7e46
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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