HCID 59442114, compound → HCID 59441783, compound

Temperature

80 °C

To a solution of 2-methyl-6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-isoquinolinone (4.7 g, 20 mmol) in THF (500 mL) was added 2.0 M BH3 in THF (49.8 mL, 100 mmol). The resulting solution was heated at reflux for 20 h. The mixture was quenched via careful addition of MeOH (50 mL), the resulting solution was concentrated under reduced pressure and the residue was heated at 80° C. with 2N HCl for 3 h. The reation was cooled, adjusted to basic pH via cautious addition of aqueous NH4OH, and extracted with dichloromethane. The combined organic layers were dried and concentrated under reduced pressure to give 6-methoxy-2-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline (3 g crude, 67%).

1. temperatureThe resulting solution was heated
2. temperatureat reflux for 20 h
3. customThe mixture was quenched via careful addition of MeOH (50 mL)
4. concentrationthe resulting solution was concentrated under reduced pressure
5. temperatureThe reation was cooled
6. additionadjusted to basic pH via cautious addition of aqueous NH4OH
7. extractionextracted with dichloromethane
8. customThe combined organic layers were dried
9. concentrationconcentrated under reduced pressure

ORD record

ord-73fdc691953647e7a86e6431c4812781

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07981903B2