Chloroform → 4-Bromo-1-methoxyisoquinoline

Participants

Reaction Steps

To a stirred suspension of 4-bromo-3-methyl-2H-isoquinolin-1-one (1.86 g, 7.81 mmol), silver carbonate (2.92 g, 10.6 mmol) and chloroform (150 mL) is added dropwise over 10 min iodomethane (7.3 mL, 117 mmol) and the mixture is stirred in the dark for 3 d. Triethylamine is added and the solids are removed by filtration through a pad of Celite. The filtrate is concentrated and the residue is purified by chromatography eluting with dichloromethane. Product containing fractions are combined and concentrated to afford 4-bromo-1-methoxyisoquinoline (1.19 g, 60% yield) as an oil that solidified on standing. LC/MS: MS m/e=252/254 (M+H); RT 4.68; 1H NMR (CDCl3, δ ppm) 8.19 (1H, d), 8.09 (1H, d), 7.71 (1H, t), 7.50 (1H, t), 4.10 (3H, s); 2.71 (3H, s).

Provenance & Evidence