2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 24967085, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 1-benzyl-6-chloro-3,4-dihydroquinazolin-2(1H)-one (0.15 g, 0.55 mmol) in DCM (5 mL) was added DDQ (0.13 g, 0.55 mmol) at 0° C. upon which the solution turned black. The mixture was stirred for 4 h at 0° C. and quenched with 1N NaOH(aq). The mixture was passed through a short path of Celite. The separated aqueous layer was extracted with DCM (2×15 mL) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a crude residue, which was purified using flash column chromatography (100% DCM to 4% MeOH in DCM gradient). The product fractions were concentrated, and washed with ether-hexanes and iPrOH successively to obtain the title compound 1-Benzyl-6-chloroquinazolin-2(1H)-one as an off-white solid. MS m/e 271 (M+H)+.

Provenance & Evidence