2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 70101852, compound

Participants

Reaction Steps

Under Ar, a solution of 19 (8.8 g, 14.1 mmol) in EtOH (270 mL) was stirred at room temperature and treated with hydrazine (1.4 g, 42.1 mmol). After 2 h, the reaction was concentrated to dryness. The reaction was partitioned between H2O and EtOAc (3×). The organic extracts were backwashed with brine, dried, filtered and concentrated to dryness. The residue was dissolved in toluene (400 mL) and treated with DDQ (3.4 g, 14.9 mmol). After stirring at room temperature for 3 h, the reaction was concentrated to dryness. The residue was chromatographed on a Still column (100 mm) and the product eluted with 60% EtOAc-hexanes to yield 5.5 g of 20.

Provenance & Evidence