1-Butyl-4,4'-bipyridin-1-ium dibromide → Acridine

Participants

Reaction Steps

A solution of 9-(2-bromomethylphenyl)acridine (1-5 mmol) and 1-butyl-4,4′-bipyridinium bromide (1-5 mmol) in the ratio of 1:1 in dry acetonitrile (30-120 mL) was stirred at 50° C. for 15h. The precipitated solid thus obtained was filtered, washed with dry acetonitrile and dichloromethane to remove any unreacted starting materials. The solid was further purified by soxhlet extraction with dichloromethane to give compound of formula 1c (wherein n=1, R=—MV2+—(CH2)3—CH3, X=Br and acridine is at the ortho position) in 35-55% yield and the product was further purified by recrystallization from ethyl acetate. Similarly, the reaction of 9-(4-bromomethyl phenyl)acridine (1-5 mmol) and 1-butyl-4,4′-bipyridinium bromide (1-5 mmol) in the ratio of 1:1 in dry acetonitrile (30-120 mL) gave compound of formula 1c (wherein n=1, R=—MV2−—(CH)3—CH3, X=Br and acridine is at the para position) in 55-70% yield and the product was further purified by recrystallization from ethyl acetate.

Provenance & Evidence