Ammonia → 5-Bromo-1-chloro-6-hydroxyisoquinoline

Participants

Reaction Steps

A solution of 1M BBr3 in dichloromethane (25.5 ml) was added dropwise to a stirred solution of 5-bromo-1-chloro-6-methoxyisoquinoline (1.26 g) in dichloromethane at 10° C. The mixture was stirred at ambient temperature for 48 h then poured into ice-water and the pH adjusted to 8 by adding concentrated aqueous ammonia. The mixture was extracted with ethyl acetate (x 2) and the aqueous phase then acidified to pH ˜4 using dilute hydrochloric acid. The aqueous phase was extracted with ethyl acetate (x 2), the combined organics were dried (Na2SO4) and concentrated in vacuo to give 5-bromo-1-chloro-6-hydroxyisoquinoline (1.1 g), El-MS: m/z=257.9, 260.0 and 261.6 [M+H]+.

Provenance & Evidence