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

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Reaction Conditions

Reaction Steps

5-Fluoro-indan-1-one (4.00 g, 26.6 mmol) was dissolved in 40 mL dichloromethane and 40 mL methanesulfonic acid. This was cooled to 0° C. and sodium azide (3.46 g, 53.2 mmol) was added. After 2 hours, the solution was made basic by slowly adding 20% aq. sodium hydroxide. The resulting mixture was partitioned between dichloromethane and water. The dichloromethane layer was dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 50 to 100% ethyl acetate/hexanes) to yield 6-Fluoro-3,4-dihydro-2H-isoquinolin-1-one (2.72 g, 16.5 mmol). MS (ESI) 166.1 (M+H)+.

Provenance & Evidence