Benzene → HCID 11298596, compound

Temperature

60 °C

Trimethylsulphonium iodide (0.954 g, 4.67 mmol) and potassium hydroxide powder (1.8 g, 32 mmol) were added to a solution of 6-methoxy-quinoline-4-carbaldehyde (0.85 g, 4.54 mmol) in acetonitrile (13.5 ml) and water (6 drops). The reaction mixture was heated at 60° C. for one hour. The mixture was then cooled to room temperature and benzene (40 ml) was added. The precipitate was filtered off and the filtrate was concentrated to dryness by rotary evaporation. The residue was diluted with water (100 ml) and ethyl acetate (100 ml), the phases were separated, and the aqueous phase was extracted twice using 50 ml of ethyl acetate each time. The combined organic phases were dried over MgSO4, filtered and concentrated to dryness by rotary evaporation. The residue was purified by column chromatography on silica gel (EtOAc).

1. temperatureThe mixture was then cooled to room temperature
2. filtrationThe precipitate was filtered off
3. concentrationthe filtrate was concentrated to dryness by rotary evaporation
4. additionThe residue was diluted with water (100 ml) and ethyl acetate (100 ml)
5. customthe phases were separated
6. extractionthe aqueous phase was extracted twice
7. dry with materialThe combined organic phases were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated to dryness by rotary evaporation
10. customThe residue was purified by column chromatography on silica gel (EtOAc)

ORD record

ord-a58aa0c01b634996be0b55141b9757e8

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223776B2