Ammonia → 1-Aminoisoquinolin-6-ol

Participants

Reaction Steps

A solution of boron tribromide (18.2 mL; 370 mmol) in 20 mL of dichloromethane was added dropwise to a stirred solution of 1-amino-6methoxy-isoquinoline (1d, 11.0 g; 63 mmol) in 150 mL of dichloromethane at 10° C. After stirring for 4 d at ambient temperature the reaction mixture was poured into ice and the pH was adjusted to 9 by adding concentrated aqueous ammonia. The precipitated material was collected by filtration and dried in vacuo to give 8.9 g (88%) of the title compound as a white solid; m.p. 258-260° C.; El-MS: 160 (M+). 1H NMR (DMSO-d6): δ 8.11 (d, 1H), 7.65 (d, 1H), 6.99 (dd, 1H), 6.86 (d, 1H), 6.80-6.63 (m, 4H), 5.2 (bs, 1H).

Provenance & Evidence