Ammonia → 7-Bromo-1-Chloroisoquinoline

Participants

Reaction Conditions

Reaction Steps

To phosphorus oxychloride (46.6 mL, 0.5 mol) at room temperature was added, portionwise, 7-bromo-1-hydroxyisoquinoline (11.2 g, 0.05 mol). The mixture was heated to 100° C. for 90 min with rapid stirring. On cooling to room temperature, the mixture was poured, cautiously onto ice/water (200 mL). Dropwise addition of aqueous ammonia raised the pH=8 and the resulting precipitate was collected by filtration, washing with cold water. The solid was dried under reduced vacuum at 45° C. for 12 h. 13.86 g (115%) Beige solid isolated. 1H NMR (DMSO-d6) δ 8.4 (s, 1H), 8.34-8.38 (d, J=6 Hz, 1H), 8.03-8.07 (m, 2H), 7.91-7.96 (d, J=6 Hz, 1H); HPLC: 96%; LCMS: 242, 244, 246.

Provenance & Evidence