4-(3-nitrophenyl)pyridine → 3-(4-Pyridyl)aniline

HRID 1628267Notes

Reaction equation

HRID 1628267 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[N:13]1[CH:14]=[CH:15][C:10]([C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 4595574-(3-nitrophenyl)pyridine

Product 1

HCID 4595233-(4-Pyridyl)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(3-nitrophenyl)pyridine 34.1.B. (500 mg, 2.9 mole) in 5 ml of methanol was added 1 g of 10% Pd on carbon by weight. The air was evacuated from the reaction flask and was replaced with hydrogen. The resulting slurry was stirred overnight at room temperature, at which time the reaction mixture was filtered over a bed of celite and the mother liquor concentrated to afford 3-(pyridin-4-yl)benzenamine 34.1.C (500 mg, 100% yield).

Workup

  1. customThe air was evacuated from the reaction flask
  2. filtrationwas filtered over a bed of celite
  3. concentrationthe mother liquor concentrated

Sources & evidence

ORD record
ord-216a4d26cd0b4dc7b7d11afcfc306b64
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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