反应详情

1,4-Diazabicyclo[2.2.2]octane (345 mg, 3.07 mmol, 0.25 eq) is added at room temperature to a stirred suspension of 3-hydroxy-6-methoxy-quinoline-4-carbaldehyde (2.5 g, 12.3 mmol, 1.0 eq) in acrylonitrile (25 mL) and the resulting mixture is heated under reflux for 60 hours. The reaction mixture is then cooled to room temperature and extracted with ethyl acetate (3×100 mL) and a 1N sodium hydroxide aqueous solution (50 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: hexane:ethyl acetate, 5:1, v/v) to afford 6-methoxy-2H-1-oxa-9-aza-phenanthrene-3-carbonitrile as a light yellow solid (2.3 g, 78% yield).

1. temperaturethe resulting mixture is heated
2. temperatureunder reflux for 60 hours
3. extractionextracted with ethyl acetate (3×100 mL)
4. dry with materialThe combined organic layers are dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a residue that
8. customis purified by column chromatography (silica gel, eluent