Phosphorus oxychloride → 1-Chloro-6-ethoxyisoquinoline

Temperature

110 °C

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).

1. custom(clear solution obtained upon heating)
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. additionThe residue was poured into iced water (10 mL)
4. extractionthe mixture extracted with chloroform (3×25 mL)
5. washThe combined chloroform layers were washed with brine
6. dry with materialdried over magnesium sulfate
7. filtrationThe organic layer was then filtered
8. concentrationconcentrated under reduced pressure

ORD record

ord-37e211e471ad46f1ac661e27fb972608

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211897B2