Tetrafluoroboric acid → HCID 67214909, compound

Participants

Reaction Steps

A mixture of 3-bromo-6-methoxy-quinolin-8-ylamine (preparation described in Journal of Pharmaceutical Sciences (1984), 73(12), 1854-6) (5.0 g) in 20 ml fluoroboric acid, (50 wt % solution in water) at ˜5° C. was treated with a solution of sodium nitrite (1.9 g in 3 ml of water) over a period of 40 minutes. The reaction mixture was stirred at room temperature for 2 hours after which time the precipitate was filtered and washed with cold diethyl ether. The resulting brown powder was added portionwise to hot dichlorobenzene over 1.5 hours. Stirring was then continued for an additional 30 min at 190° C. On cooling to room temperature, the mixture was treated with dilute hydrochloric acid and diluted with ethyl acetate. The organic phase was washed with dilute sodium hydroxide, dried over sodium sulphate, filtered and evaporated under reduced pressure to give a black oil that was fractionated by chromatography (silica; cyclohexane/ethyl acetate) to give the required product (M+256)

Provenance & Evidence