3-Methoxymethyl-5-nitroisoquinoline → 5-Amino-3-methoxymethylisoquinoline

Participants

Reaction Steps

A catalyst (3% palladium-on-charcoal; 8 g) is added to a solution of 3-methoxymethyl-5-nitroisoquinoline (78 g) in ethanol (2 liters). The resulting suspension is stirred and hydrogen is bubbled through for 6 hours, whilst keeping the temperature between 20° and 25° C. with the aid of a bath of cold water. The mixture is then filtered and the filtrate is evaporated to dryness at 60° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is recrystallised from diisopropyl ether (500 cc). 5-Amino-3-methoxymethylisoquinoline (47 g), m.p. 105° C., is obtained.

Provenance & Evidence