2-(3-Nitrophenyl)pyridine → 3-(2-Pyridyl)aniline

HRID 581929Notes

Reaction equation

HRID 581929 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>[Pd].C(O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1]

Participants

5

Reactant 2

HCID 4595552-(3-Nitrophenyl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 4595173-(2-Pyridyl)anilineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(3-nitrophenyl)pyridine (prepared as described in J. Chem. Soc. 1958 p. 1759) (12.7 g, 63.5 mmol) in abs. ethanol is added palladium catalyst (1.3 g 5% Pd on activated carbon) and the mixture is hydrogenated at ambient pressure until the hydrogen uptake has ceased. The mixture is filtered through celite and the filtrate is concentrated under reduced pressure. The residue is purified by column-chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (9:1) as the eluent to afford 2f (9.5 g, 88%) as a light brown oil.

Workup

  1. filtrationThe mixture is filtered through celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by column-chromatography on silica gel using
  4. additiona mixture of ethyl acetate and petroleum ether (9:1) as the eluent

Sources & evidence

ORD record
ord-c560b47ac9cf41dea241c965f4ff3c10
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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