3-(3-Nitrophenoxy)pyridine → 3-(Pyridin-3-yloxy)aniline

HRID 1696434Notes

Reaction equation

HRID 1696434 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)([O-])=O>CCOC(C)=O.O=[Pt]=O>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:16]=[CH:15][CH:14]=2)[CH:9]=1

Participants

4

Reactant 1

HCID 212855723-(3-Nitrophenoxy)pyridine

Product 1

HCID 212855823-(Pyridin-3-yloxy)anilineYield 99%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3-nitrophenoxy)pyridine (4.43 g, 20.5 mmol) in EtOAc (50 mL) was added PtO2 (0.4 g) and the mixture was stirred at RT overnight under H2 (1 atm). The mixture was filtered through Celite®, the Celite® washed with EtOAc (2×20 mL) and the combined filtrates concentrated to yield (3.77 g, 99% yield) pure 3-(pyridin-3-yloxy)benzenamine as a syrup. 1H NMR (400 MHz, DMSO-d6): δ 8.34-8.32 (m, 2H), 7.40-7.39 (m, 2H), 7.02 (t, J=8.0 Hz, 1H), 6.37-6.35 (m, 1H), 6.02-6.14 (m, 2H), 5.28 (brs, 2H); MS (ESI) m/z: 187.0 (M+H+).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washthe Celite® washed with EtOAc (2×20 mL)
  3. concentrationthe combined filtrates concentrated

Sources & evidence

ORD record
ord-09377eca088d47899f189386fb06bae7
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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