Ammonium Chloride → HCID 21710454, compound

Participants

Reaction Steps

To solution of 5-aminoisoquinoline (15 g, 104 mmol) in acetone (400 ml) was added benzyl bromide (18.6 ml, 156 mmol). The mixture was stirred at room temp for 2 h before the precipitate was filtered off affording an orange solid (8.64 g). A second crop (4.02 g) was filtered after a further 2 h. To a solution of this 5-amino-2-benzyl-isoquinolinium bromide (8.46 g, 26.8 mmol) in THF (75 ml) at 0° C. under argon was added dropwise methyl magnesium chloride (17.89 ml, 56.6 mmol). The mixture was allowed to warm up to room temperature and was stirred for 2 h. The mixture was then poured into ammonium chloride solution and extracted with ether. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford the title compound as a light brown solid (5.0 g).

Provenance & Evidence