2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178516364, compound

Participants

Reaction Steps

To 1 g of 2,3-Dihydrobenzo[g]quinolin-4(1H)-one (5) (5.07 mmol) in 20 mL of toluene (0.25 M) under a nitrogen atmosphere was added 1.5 g of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ, 1.3 equivalents). The reaction mixture was heated to reflux and monitored by TLC until completion (approximately 2 h). After cooling to rt, the mixture was concentrated in vacuo then filtered through a silica plug using 10% methanol in methylene chloride to afford crude phenol (6). Subsequently, the crude phenol was directly subjected to the halogenation conditions of step 2.

Provenance & Evidence