Pyridine (5-methyl-2-nitrophenyl)nitride → 2-amino-5-methyl-N-(2-pyridyl)aniline

HRID 50935Notes

Reaction equation

HRID 50935 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([CH:14]=1)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1>[Pd].C(O)C>[NH2:15][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:14][C:6]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 1

HCID 556627Pyridine (5-methyl-2-nitrophenyl)nitride

Product 1

HCID 227367082-amino-5-methyl-N-(2-pyridyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-methyl-2-nitro-N-(2-pyridyl)aniline (3.8 g, 16.6 mmol), 5% palladium on carbon (500 mg) in ethanol (100 ml) was stirred under a hydrogen atmosphere for 3 h. The mixture was filtered through a pad of celite and the filtrate was concentrated to dryness to give 3.3 g (quant.) of the titled compound as gray solids. 1H-NMR (CDCl3) δ: 8.17-8.10 (1H, m), 7.46-7.38 (1H, m), 7.00 (1H, s), 6.90 (1H, d, J=8.1 Hz), 6.76-6.62 (2H, m), 6.46-6.39 (1H, m), 6.29 (1H, br.s), 3.71 (2H, br.s), 2.24 (3H, s).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-d9b63b2bf03a48bd9dbb2c8208776ce6
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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