N-(2-(benzyloxy)phenyl)-3-fluoroisonicotinamide → 3-fluoro-N-(2-hydroxyphenyl)isonicotinamide

Participants

Reaction Steps

Title compound 24 (4.40 g, 13.6 mmol) was dissolved in 33% HBr in AcOH (30 mL) and the reaction mixture was stirred at room temperature for 2 hours. The mixture was diluted with water and solid sodium bicarbonate (until alkaline) then extracted twice with ethyl acetate. The combined organic extracts were washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The crude was triturated in 30% ethyl acetate in hexanes to afford the title compound 25 (2.36 g, 75%) as a beige solid. LRMS (ESI): (calc) 232.06 (found) 233.1 (MH)+.

Provenance & Evidence