Sodium Hydroxide → 5-Bromoisoquinoline

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) solution of HBr-H2O (48%) (10 ml) in water (30 ml) was added 5-aminoisoquinoline (5 g; 35 mmol) followed by sodium nitrite (2.4 g; 35 mmol) in water (20 ml). The mixture was added to a warm (75° C.) solution of cuprous bromide (5 g; 35 mmol) in HBr-H2O (48%) (50 ml) and stirred overnight at 75° C. The reaction mixture was cooled, basified to pH11 with NaOH (5 M) and steamed distilled to afford the title compound (1.4 g) as a colourless crystalline solid (mp 65° C.).

Provenance & Evidence