Hydrochloric Acid → 6-tert-butyl-2-[3-chloro-2-(hydroxymethyl)phenyl]-8-(hydroxymethyl)phthalazin-1(2H)-one

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Reaction Steps

The above 7-tert-butyl-3-[3-chloro-2-(hydroxymethyl)phenyl]-4-oxo-3,4-dihydrophthalazine-5-carbaldehyde (147 mg, 0.396 mmol) was combined with dichloroethane (5 mL) and methanol (5 mL) to give a yellow solution. Sodium borohydride (27 mg, 0.714 mmol) was added and the mixture was stirred at room temperature for 4 hrs. The mixture was treated with 1N hydrochloric acid and extracted with dichloromethane. The organic layer was washed with brined and dried over sodium sulfate. After the evaporation of solvents, the residue was purified by flash column chromatography (silica gel 40 g, 0% to 40% ethyl acetate in heptane) to give 6-tert-butyl-2-[3-chloro-2-(hydroxymethyl)phenyl]-8-(hydroxymethyl)phthalazin-1(2H)-one as a light yellow solid (39 mg, 26.4%). LC/MS calcd for C20H21ClN2O3 (m/e) 372.12, obsd 371.1 (M−H, ES−).

Provenance & Evidence