Water → HCID 178429660, compound

Temperature

50 °C

A stirred suspension of 2-methylquinolin-4-ol (5.10 g, 32.0 mmol, 1.0 eq.) in tetrahydrofuran (51 mL) was heated to 50° C., and 6.5 g of Lawesson's Reagent (6.5 g, 16.0 mmol, 0.5 eq.) was added in one portion. The reaction was heated to 80° C. and stirred at that temperature for 6 hours. The reaction was poured into a hot biphasic solution of ethyl acetate (200 mL) and water (200 mL) and was vigorously stirred. A viscous orange gel precipitated from the solution. The water/ethyl acetate solution was decanted into a separating funnel and the organic layer isolated. The aqueous layer was extracted with ethyl acetate (4×200 ml), and the combined extracts were dried over magnesium sulfate. The solution was filtered and concentrated in vacuo. The resulting orange gel was purified by flash chromatography (50% EtOAc:50% petroleum ether→100% EtOAc) to yield 5a as a yellow solid (1.70 g, 30%).

1. temperatureThe reaction was heated to 80° C.
2. stirringwas vigorously stirred
3. customA viscous orange gel precipitated from the solution
4. customThe water/ethyl acetate solution was decanted into a separating funnel
5. customthe organic layer isolated
6. extractionThe aqueous layer was extracted with ethyl acetate (4×200 ml)
7. dry with materialthe combined extracts were dried over magnesium sulfate
8. filtrationThe solution was filtered
9. concentrationconcentrated in vacuo
10. customThe resulting orange gel was purified by flash chromatography (50% EtOAc:50% petroleum ether→100% EtOAc)

ORD record

ord-8f7d3a7daea74eebb0d3c6d03ff421ef

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786139B2