4-(Benzyloxy)-3-nitropyridine → 4-(Benzyloxy)pyridin-3-amine

HRID 44109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 44109
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N+:15]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C1COCC1.[Ni]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 127165204-(Benzyloxy)-3-nitropyridineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 288900524-(Benzyloxy)pyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(benzyloxy)-3-nitropyridine (15 g, 65 mmol, 1 eq) was dissolved in THF, then Raney Nickel (2.25 g, 10% w/w) (washed with THF) was added under nitrogen atmosphere and the reaction was stirred at room temperature with 2 kg hydrogen pressure for 6 h. The reaction solution was filtered through celite and the filtrate was concentrated under vacuum to get brown oil. The product was taken to the next step without purification. Yield: 12.3 g (94%). 1HNMR (400 MHz, DMSO-d6): δ 4.86 (s, 2H), 5.18 (s, 2H), 6.88 (d, 1H, J=5.32 Hz), 7.31 (t, 1H, J=3.90 Hz), 7.4 (t, 2H, J=5.08 Hz), 7.5 (t, 2H, J=8.08 Hz), 7.71 (d, J=2.05 Hz, 1H), 7.89 (s, 1H).

Aufarbeitung

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto get brown oil
  4. customThe product was taken to the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-ca94dd1619f34c558e110a8f8237a65f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536338B2

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