O-ethylhydroxylamine hydrochloride → 1-ethoxy-1H-imidazo[4,5-c]quinoline
Reaktionsgleichung
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][CH:13]=O.Cl.[CH2:16]([O:18][NH2:19])[CH3:17]>C(O)(C)C>[CH2:16]([O:18][N:19]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=[CH:13]1)[CH3:17]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 4-chloroquinolin-3-ylformamide (5.0 g, 24 mmol), O-ethylhydroxylamine hydrochloride (2.95 g, 30.2 mmol), and isopropanol (75 mL) was heated at reflux overnight, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was stirred with dichloromethane (150 mL) and saturated aqueous sodium carbonate (50 mL) for 15 minutes. The organic layer was separated and dried over potassium carbonate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 2% methanol in dichloromethane containing 5 mL of aqueous ammonium hydroxide per liter of eluent) to provide 2.45 g of 1-ethoxy-1H-imidazo[4,5-c]quinoline.
Aufarbeitung
- temperatureat reflux overnight
- concentrationconcentrated under reduced pressure
- customThe organic layer was separated
- dry with materialdried over potassium carbonate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by column chromatography on silica gel (eluting with 2% methanol in dichloromethane containing 5 mL of aqueous ammonium hydroxide per liter of eluent)
Quellen und Nachweise
- ORD-Eintrag
- ord-a91af1a69f174bea8db4f7f02889b41c
- Quelldatensatz
- uspto-grants-2009_08
- Patentnummer
- US07579359B2
Notizen zur Reaktion
Wird geladen…