2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(3-Chloropropyl)-7-methyl-1H-quinolin-2-one

Participants

Reaction Steps

A microwave vial was charged with 1-(3-chloropropyl)-7-methyl-3,4-dihydro-1H-quinolin-2-one (0.21 g, 0.88 mmol), DDQ (0.30 g, 1.3 mmol), dioxane (4 mL) and sealed. After microwave irradiation, 175° C., 10 min, the reaction was diluted with EtOAc (50 mL), washed with sat aqueous NaHCO3 (2×15 mL) and the organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified with prep RP-HPLC to yield the crude title compound (0.130 g), which was used without further purification. HPLC-MS (ammonium acetate) [M+H]+=236.2.

Provenance & Evidence