2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Agomelatine

Participants

Reaction Steps

To a solution of the compound obtained in Step E (100 mg, 0.41 mmol) in dichloromethane (4 mL) there is added, at ambient temperature, DDQ (111 mg, 0.49 mmol). The reaction mixture is stirred for 2 days and then washed with saturated NaHCO3 solution. The aqueous phase is extracted with ethyl acetate, and the organic phases are collected and then dried using brine and then over MgSO4. After filtration, the solvents are evaporated off under reduced pressure and the crude reaction mixture obtained is purified by chromatography on a silica column (eluant: ethyl acetate/petroleum ether 90/10, then ethyl acetate/methanol 90/10) to yield the title product in a yield of 48%.

Provenance & Evidence