Phosphorus oxychloride → 1-Chloro-6-ethoxyisoquinoline
Reaktionsgleichung
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=O)[NH:9][CH:8]=[CH:7]2)[CH3:2].P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:10]1[C:11]2[C:6](=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:13][CH:12]=2)[CH:7]=[CH:8][N:9]=1Komponenten
3
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
A suspension of 6-ethoxy-2H-isoquinolin-1-one (896 mg, 4.74 mmol) in phosphorus oxychloride (POCl3, 4 mL) was heated at 110° C. for 3 hours (clear solution obtained upon heating). After 3 hours, the reaction mixture was concentrated under reduced pressure. The residue was poured into iced water (10 mL), the pH adjusted to 10 with 3N sodium hydroxide, and the mixture extracted with chloroform (3×25 mL). The combined chloroform layers were washed with brine and dried over magnesium sulfate. The organic layer was then filtered and concentrated under reduced pressure to give 1-chloro-6-ethoxy-isoquinoline (866 mg, 4.18 mmol, 88% yield, >90% pure) as tan solid. MS m/z 208 (M++H).