Acetic Acid → 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one

Participants

Reaction Steps

1.2 g (5.4 mmol) of 5-tert-butyl-7-fluoro-3-hydroxy-3H-isobenzofuran-1-one was weighed into a 25 mL round bottom flask fitted with a stir bar, condenser, and nitrogen inlet. Added 7.5 mL (100 mmol) of hydrazine monohydrate. Added 10 mL of glacial acetic acid. Stirred under nitrogen at 100° overnight. Poured the reaction mixture into 100 ml, of stirred water. Extracted the aqueous mixture with 2×50 mL CH2Cl2. Dried the combined extracts over Na2SO4 and removed the solvent on the rotavap. Purified by silica gel flash chromatography using gradient elution with 0→100% EtOAc/CH2Cl2 to obtain 898 mg of the title compound as an off-white solid. MS (ESI) 221 (M+H)+.

Provenance & Evidence