4-(4-Nitrophenyl)pyridine → 4-(Pyridin-4-yl)aniline

HRID 332777

Reaction equation

HRID 332777 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[N:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 2592194-(4-Nitrophenyl)pyridine

Product 1

HCID 15126544-(Pyridin-4-yl)anilineYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(4-nitrophenyl)pyridine (274 mg, 1.37 mmol) and Pd—C(10%, 80 mg) in MeOH (10 mL) was hydrogenated under balloon H2 for 20 h. The mixture was then filtered through celite. The filtrate was concentrated in vacuo to give 4-(pyridin-4-yl)aniline as a solid (211 mg).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b136c50eebdc4587874f3fe657e9b211
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Linked notes

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