Hydrochloric Acid → HCID 51198164, compound

To a solution (50 mL) of 1-(5-chloro-2-hydroxyphenyl)ethanone (5.00 g) in tetrahydrofuran were added potassium carbonate (8.10 g), sodium iodide (8.78 g) and 2-chloro-N-methoxy-N-methylacetamide (4.43 g), and the mixture was stirred overnight with heating under reflux. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give a white solid. To a solution (50 mL) of the obtained solid in N,N-dimethylformamide was added 1,8-diazabicyclo[5.4.0]undec-7-ene (4.38 mL), and the mixture was stirred at 120° C. for 2 hr. The reaction mixture was cooled to room temperature, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to give the title object compound (2.15 g, 29%) as a brown solid.

1. temperaturewith heating
2. temperatureunder reflux
3. filtrationInsoluble material was filtered off
4. concentrationthe filtrate was concentrated under reduced pressure
5. customto give a white solid
6. stirringthe mixture was stirred at 120° C. for 2 hr
7. extractionthe mixture was extracted with ethyl acetate
8. washThe extract was washed with saturated brine
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

ORD record

ord-6f9d3a052d3b4028918fd880186e4a30

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2