Sodium Hydroxide → 6-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one

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Reaction Steps

Sodium azide (7.8 g, 120 mmol) was added portionwise to a stirred solution of 5-fluoro indanone (9 g, 60 mmol) in methanesulfonic acid (35 mL) and dichloromethane (35 mL), while the temperature was maintained between 22°-29° C. Once addition was completed, the mixture was stirred at room temperature for 16 hours. The mixture was cooled to 0° C. and neutralized by the addition of 5N-NaOH solution and the organic layer separated. The aqueous layer was washed with dichloromethane (3×50 mL) and the combined organics washed with water (50 mL), brine (50 mL) and dried over anhydrous sodium sulfate. Filtration and concentration gave a light oil (7.8 g) which was purified by flash silica gel chromatography (eluted with diethyl ether) to afford the titled compound as a white solid.

Provenance & Evidence