3-(3-Nitrophenyl)pyridine → 3-(Pyridin-3-yl)aniline

HRID 1696531Notes

Reaction equation

HRID 1696531 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CCOC(C)=O.O=[Pt]=O>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)[CH:11]=1

Participants

4

Reactant 1

HCID 121813273-(3-Nitrophenyl)pyridine

Product 1

HCID 4595213-(Pyridin-3-yl)anilineYield 94%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3-nitrophenyl)pyridine (0.22 g, 1.1 mmol) in EtOAc (10 mL) was added PtO2 (0.025 g, 10% mol) and the mixture was stirred for 4 h under H2 (1 atm). It was filtered through Celite® and the combined filtrates were concentrated to yield 3-(pyridin-3-yl)benzenamine (0.175 g, 94%) as a semi solid which was used without further purification. 1H NMR (DMSO-d6): 8.77 (d, J=2.0 Hz, 1H), 8.53 (dd, J=8.8 Hz, 1.6 Hz, 1H), 7.57-7.52 (m, 1H), 7.46-7.43 (m, 1H), 7.13 (t, J=8.0 Hz, 1H), 6.86-6.80 (m, 2H), 6.63-6.60 (m, 1H), 5.23 (s, 2H); Exact mass: 170.0, Found: 171.0 (M+1)+.

Workup

  1. filtrationIt was filtered through Celite®
  2. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-8c36a06f57024cbcb704d1e3e22794fb
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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