Phosphorus trichloride → HCID 11264890, compound

To 6-(2-methoxyethoxy)isoquinolin-1-ol (3.15 g, 14.4 mmol) was added phosphorus trichloride (70 mL) under nitrogen atmosphere. The mixture was heated at reflux giving a nearly opaque brown solution. After 2 h at reflux, the solution was concentrated in vacuo until 20 mL remained and poured onto ice water (100 mL). The pH of the resulting mixture was adjusted to 6.5 with the addition of solid potassium carbonate and extracted with dichloromethane (3×100 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL) and concentrated in vacuo. The resulting tan solid was taken up in dichloromethane, adsorbed on silica gel and purified by flash chromatography (gradient:hexane/ethyl acetate, 60:40→40:60) to give, after drying in vacuo, 2.73 g (80% yield) of the title compound as a pale yellow solid. MS(AP+), 238 (100, M++1), 202 (33), 179 (33).

1. temperatureThe mixture was heated
2. temperatureat reflux
3. customgiving a nearly opaque brown solution
4. temperatureAfter 2 h at reflux
5. concentrationthe solution was concentrated in vacuo until 20 mL
6. additionpoured onto ice water (100 mL)
7. additionThe pH of the resulting mixture was adjusted to 6.5 with the addition of solid potassium carbonate
8. extractionextracted with dichloromethane (3×100 mL)
9. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
10. concentrationconcentrated in vacuo
11. custompurified by flash chromatography (gradient:hexane/ethyl acetate, 60:40→40:60)
12. customto give

ORD record

ord-830d820a48324c95aa835f51e9bec2eb

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07205314B2