Ammonium Acetate → 6-Methoxyisoquinolin-1-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-methoxy-1-phenoxyisoquinoline (21.3 g, 85 mmol) and ammonium acetate (55 g) was heated, under a nitrogen atmosphere, to 150° C. and stirred overnight. The mixture was allowed to cool to ambient temperature, after which 3 N sodium hydroxide (280 ml) was added with stirring. The thus obtained solution was extracted with ethyl acetate (2×300 ml) and the combined organic layers were extracted with 2N hydrochloric acid (100 ml). Subsequently, the pH of the aqueous layer was adjusted to 12 with 2 N sodium hydroxide. Extraction with ethyl acetate (300 ml) then afforded an organic layer, which was washed with brine (100 ml), dried (magnesium sulphate) and concentrated under reduced pressure to give 1-amino-6-methoxyisoquinoline (11 g, 75%), ESI-MS: 175.2 [M+H]+

Provenance & Evidence