Chloranil → HCID 23085645, compound

Participants

Reaction Steps

2-Phenyl-6-nitro-3,4-dihydroquinazoline (27 g, 0.106 mol) and chloranil (32.4 g, 0.13 mol) in toluene (450 ml) are refluxed for 60 minutes. The mixture is cooled to room temperature, and the precipitate is filtered off and washed with toluene (350 ml). The filtrate is suspended in 0.5N NaOH (400 ml) and the aqueous phase is extracted with dichloromethane (100 ml). The combined organic phases are washed with water and concentrated. The solid is recrystallized from hexane. Yield: 8.8 g (34%); Rf (8/2 petroleum ether/ethyl acetate): 0.71; 1H-NMR (d6-DMSO) 9.91 (s, 1H); 9.18 (d, 1H); 8.61 (m, 3H); 8.24 (d, 1H); 7.55 (m, 3H).

Provenance & Evidence