2-{1-(Methoxycarbonyl)ethoxy}-3-nitropyridine → 3-Amino-2-{1-(methoxycarbonyl)ethoxy}pyridine

HRID 493957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 493957
[CH3:1][O:2][C:3]([CH:5]([O:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:6])=[O:4]>[Pt]=O.C(O)C>[NH2:14][C:13]1[C:8]([O:7][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6])=[N:9][CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 1

HCID 219335712-{1-(Methoxycarbonyl)ethoxy}-3-nitropyridine

Produkt 1

HCID 219335303-Amino-2-{1-(methoxycarbonyl)ethoxy}pyridineAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1.7 g of 2-{1-(methoxycarbonyl)ethoxy}-3-nitropyridine, 102 mg of platinum oxide, and 7.5 ml of ethanol was stirred at room temperature under an atmosphere of hydrogen gas for 3.5 hours. The gas in the atmosphere on the reaction system was replaced with nitrogen gas, and the reaction mixture was filtered through Celite. The filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 1.16 g of 3-amino-2-{1-(methoxycarbonyl)ethoxy}pyridine. 1H-NMR (CDCl3, 300 MHz) δ(ppm): 1.63 (d, 3H, J=6.8 Hz), 3.74 (s, 3H), 3.84 (bs, 2H), 5.38 (d, 1H, J=6.8 Hz), 6.72 (dd, 1H, J=7.7, 5.0 Hz), 6.90 (dd, 1H, J=7.7, 1.4 Hz), 7.48 (dd, 1H, J=5.0, 1.4 Hz).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2d8d7b8517e443b7b63e420f80aa4fa2
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538072B2

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