Ammonia → 1-Aminoisoquinolin-6-ol

Participants

Reaction Steps

A solution of boron tribromide (18.2 ml, 370 mmol) in 20 ml dichloromethane was added dropwise to a stirred solution of 1-amino-6-methoxyisoquinoline (11.0 g, 63 mmol) in 150 ml of dichloromethane at 10° C. After stirring for 4 days 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 1-amino-6-hydroxyisoquinoline (8.9 g, 88%), EI-MS: 160 [M]+

Provenance & Evidence