4-(6-Nitropyridin-3-yl)morpholine → 5-Morpholinopyridin-2-amine

HRID 272487

Reaktionsgleichung

Reaktionsgleichung von HRID 272487
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>C1COCC1.[Ni]>[N:10]1([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[N:9][CH:8]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Komponenten

4

Edukt 1

HCID 29279734-(6-Nitropyridin-3-yl)morpholine

Produkt 1

HCID 113673465-Morpholinopyridin-2-amineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(6-Nitro-pyridin-3-yl)-morpholine (2.86 g, 13.7 mmol) was dissolved in THF (100 mL) to which Raney Nickel (1.03 g) was added. The reaction mixture was shaken under a hydrogen atmosphere (50 psi) for 4 hours. The catalyst was removed by filtration and the solvent evaporated to give 5-morpholin-4-yl-pyridin-2-ylamine as a purple solid (1.91 g, 78.0%). 1H NMR δ(400 MHz, CDCl3) 7.76 (d, J=2.0 Hz, 1H), 7.16 (dd, J=2.7, 8.8 Hz, 1H), 6.50 (d, J=8.8 Hz, 1H), 4.24 (s, 2H), 3.84 (m, 4H), 3.16 (m, 4H), 3.01 (m, 4H).

Aufarbeitung

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f3fa3ff91d02495c9139bc7fdb6bf298
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456168B2

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