6-bromo-N-methoxy-N-methylquinoline-2-carboxamide → 1-(6-Bromoquinolin-2-yl)ethanone
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12](N(OC)C)=[O:13])[CH:6]=[CH:5]2.[CH3:18][Mg]Br>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12](=[O:13])[CH3:18])[CH:6]=[CH:5]2Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 6-bromo-N-methoxy-N-methylquinoline-2-carboxamide (4.29 g, 14.5 mmol) in THF (100 ml) was added methyl magnesiumbromide (18.2 ml, 17.4 mmol, 0.96M in THF solution) at 0° C. dropwise and the mixture was stirred at 0° C. for 1 hour. Then, the mixture was quenched with saturated ammonium chloride aqueous solution (50 ml) and water (200 ml). After stirring for 30 min, the product was extracted with ethyl acetate which was dried over sodium sulfate. Then, filtration, evaporation and purification through silica gel column chromatography, eluting with hexane/ethyl acetate (4:1), furnished the title compound (3.47 g, 96% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 2.66 (3H, s), 7.83-7.88 (1H, m), 8.02-8.20 (4H, m). MS (ESI): m/z 250, 252 (M+H)+.
Aufarbeitung
- customThen, the mixture was quenched with saturated ammonium chloride aqueous solution (50 ml) and water (200 ml)
- stirringAfter stirring for 30 min
- extractionthe product was extracted with ethyl acetate which
- dry with materialwas dried over sodium sulfate
- filtrationThen, filtration, evaporation and purification through silica gel column chromatography
- washeluting with hexane/ethyl acetate (4:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-5c2f439e379a49cfbcc06e98510a5a17
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08158650B2
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