Chromic Acid → 3-(5-Fluoro-4-keto-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline

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Reaction Steps

Chromic acid (4.9 g) was added to an acetic acid (50 mL) solution of 3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (5.0 g, 16.4 mmol), followed by heating and refluxing for 14 hours, pouring water, aqueous sodium sulfite solution and aqueous sodium hydrogencarbonate solution. After stirring for 30 minutes, extracting with ethyl acetate, and applying the resulting residue to chromatography to obtain 0.3 g (yield 6%) of the target compound.

Provenance & Evidence