Methane, dichloromethoxy- → HCID 21931682, compound

To a flame dried round bottom flask equipped with a nitrogen cap was added 180 mg (1.35 mmol) aluminum chloride and 10 ml of methylene chloride. The mixture was stirred at ambient temperature for 0.25 hour and then cooled to 0° C. followed by the addition of 177 mg (0.69 mmol) 1-methanesulfonyl-6-methoxy-3,4-dihydro-1H-quinolin-2-one. The reaction mixture was stirred for 10 minutes at this temperature and was then treated with 171 μl (1.89 mmol) of α,α-dichloromethyl methyl ether before allowing the reaction to slowly warm to room temperature over 16 hours. The reaction mixture was quenched with 30 ml of 2M HCl and extracted with ethyl acetate (3×30 ml). The combined organics were then washed with saturated aqueous bicarbonate solution and brine followed by drying over sodium sulfate and evaporation in vacuo. The crude residue was purified on silica gel eluting with 95/5 methylene chloride/methanol to afford an off white solid in 66% yield (130 mg). Mass spectrum APCI m/e 284 (p+1).

1. customTo a flame dried round bottom flask
2. customequipped with a nitrogen
3. customcap
4. temperaturecooled to 0° C.
5. stirringThe reaction mixture was stirred for 10 minutes at this temperature
6. customthe reaction
7. temperatureto slowly warm to room temperature over 16 hours
8. customThe reaction mixture was quenched with 30 ml of 2M HCl
9. extractionextracted with ethyl acetate (3×30 ml)
10. washThe combined organics were then washed with saturated aqueous bicarbonate solution and brine
11. dry with materialby drying over sodium sulfate and evaporation in vacuo
12. customThe crude residue was purified on silica gel eluting with 95/5 methylene chloride/methanol
13. customto afford an off white solid in 66% yield (130 mg)

ORD record

ord-81c95d9cbb40485891678c7706586d9a

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119207B2