1,4-Dichlorophthalazine → 1-(4-Chlorophthalazin-1-yl)-7-methoxynaphthalen-2-ol

Participants

Reaction Steps

In a 1 L flask under nitrogen were mixed 1,4-dichlorophthalazine (11.4 g, 57.3 mmol) with 7-methoxy-naphthalen-2-ol (10.0 g, 57.5 mmol). To this was added 1,2-dichloroethane (450 ml). After stirring for 10 min, aluminum chloride (7.64 g, 57.4 mmol) was added. The resulting suspension was stirred for 20 hrs at 80° C. After cooling to room temperature, the black suspension was poured on ice-water (500 ml) and stirred for 1 hr. The two layers were separated. The aqueous layer was extracted with dichloromethane (3×200 ml). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The crude solid was triturated with dichloromethane (35 ml) for 1 hr and collected by filtration to give 15.2 g of the title compound as a grey solid. (Yield: 80%)

Provenance & Evidence