Methanol → 6-(Oxazol-5-yl)isoquinoline

Participants

Reaction Conditions

Reaction Steps

To a 150 mL round-bottomed flask was added p-toluenesulfonylmethyl isocyanide (3.50 g, 18.0 mmol) and MeOH, followed by sodium methoxide (11.0 mL, 50.9 mmol) and a MeOH solution of isoquinoline-6-carbaldehyde (2.35 g, 15.0 mmol). The solution was stirred at reflux for about 1 hour and followed by LCMS. Water was added (50 mL) and the MeOH was removed in vacuo. The suspension was cooled to 0° C., and the resulting precipitate was filtered and dried in a vacuum oven overnight to give 6-(oxazol-5-yl)isoquinoline (2.50 g, 85% yield) as a tan powder. LCMS (API-ES) m/z (%): (100%, M++H).

Provenance & Evidence