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

HRID 1696434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696434
[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

Komponenten

4

Edukt 1

HCID 212855723-(3-Nitrophenoxy)pyridine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-09377eca088d47899f189386fb06bae7
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163756B2

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