Methanol → 7-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 417921

Reaktionsgleichung

Reaktionsgleichung von HRID 417921
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1)([O-])=O.CO>[Pd].CCOC(C)=O>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1

Komponenten

5

Edukt 2

HCID 887MethanolHCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Produkt 1

HCID 27641827-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

7-Nitro-4H-benzo[1,4]oxazin-3-one (0.65 g, 3.3 mmol) and 10% palladium on carbon (0.13 g) were combined in EtOAc (15 mL) and MeOH (15 mL) and hydrogenated for 2 h at atmospheric pressure. The catalyst was removed by filtration through celite and the filtrate reduced in vacuo to yield the title compound as a colourless oil (0.50 g, 91%). δH (DMSO-d6) 4.42 (2H, s), 4.89 (2H, br s), 6.13-6.20 (2H, m), 6.56 (1H, d, J 8.1 Hz), 10.27 (1H, br s).

Aufarbeitung

  1. customThe catalyst was removed by filtration through celite

Quellen und Nachweise

ORD-Eintrag
ord-dbf68fd6059442cc92254761fb481355
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093238B2

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