Reaktionsgleichung
CC1[CH:6]=[C:5]([C:7]2[C:8](=[O:25])[NH:9][C:10]3[C:15]([C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14]C(C=O)=[CH:12][CH:11]=3)ON=1.[CH3:26][C:27]([CH3:32])([CH3:31])[CH:28]=[N:29][OH:30].Cl[O-:34].[Na+].[CH2:36]([Cl:38])Cl>>[C:16]([C:15]1[CH:14]=[C:36]([Cl:38])[CH:12]=[CH:11][C:10]=1[NH:9][C:8](=[O:25])[CH2:7][C:5]1[O:30][N:29]=[C:28]([C:27]([CH3:32])([CH3:31])[CH3:26])[CH:6]=1)(=[O:34])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To an ice-cold solution of but-3-ynoic acid (2-benzoyl-4-chlorophenyl)amide (a) (0.100 g, 0.336 mmol) in anhydrous DCM (7 mL) was added 2,2-dimethylpropionaldehyde oxime (0.204 g, 2.02 mmol) and sodium hypochlorite solution (3.50 mL). After stirring for 2 h at 0° C., the reaction was warmed to 25° C. and stirred overnight. The organic layer was separated, dried (MgSO4), and concentrated to provide N-(2-benzoyl-4-chlorophenyl)-2-(3-tert-butyl-isoxazol-5-yl)-acetamide as a yellow oil. This ketoamide was dissolved in anhydrous toluene (4 mL) and treated with triethylamine (0.5 mL). After stirring for 12 h at 25° C., the reaction mixture was evaporated to afford the crude product as a yellow oil. Purification by flash chromatography afforded 3-(3-tert-butyl-isoxazol-5-yl)-6-chloro-4-phenyl-1H-quinolin-2-one (b) (0.10 g, 77% yield) as a white solid. 1H NMR (300 MHz, CDCl3): δ 11.83 (s, 1H), 7.52-7.45 (m 4H), 7.36 (d, J=8.6 Hz, 1H), 7.26-7.20 (m, 3H), 6.42 (s, 1H), 1.26 (s, 9H). MS: 379 (M+H).
Aufarbeitung
- temperaturethe reaction was warmed to 25° C.
- stirringstirred overnight
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-bfd5bef118664020a9c7db566367ee51
- Quelldatensatz
- uspto-grants-2008_02
- Patentnummer
- US07326788B2
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