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

HRID 398387Notes

Reaction equation

HRID 398387 reaction equation
[CH:1]([C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].[H][H]>C(O)C.[Pd]>[CH2:1]([C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 118296173-Nitro-2-vinylpyridineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 218818002-Ethylpyridin-3-amineYield 57.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-vinyl-3-nitropyridine (0.75 g, 5.0 mMol) from step 1 above dissolved in 50 mL of ethanol and 100 mg of 10% palladium on carbon was shaken under 55 psi of hydrogen using a parr hydrogenation apparatus until hydrogen uptake ceased. The mixture was filtered through a bed of celite and the filtrate concentrated in vacuo. The residue was purified by flash silica gel chromatography using 1% then 2% methanol in methylene chloride as an eluent to afford the title compound as a white crystalline solid (0.35 g).

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-fd611174db2648d4b54eee7be3d3b4ba
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

Loading…