Water → 5-Methoxyisoquinoline

Participants

Reaction Steps

To an oven dry three neck flask was added 5-hydroxy-quinoline (5 g, 34.5 mmol), and triphenylphosphine. The solids were dissolved in THF (100 mL) and DEAD (8.19 mL, 51.7 mmol) was added slowly. The maroon reaction mixture was stirred at room temperature overnight and then poured into H2O (100 mL) and extracted into EtOAc (3×150 mL). The combined organic fractions were dried over Na2SO4, filtered, concentrated, and purified by column chromatography using 20% EtOAc/hexanes as the eluent. The title compound was isolated as 3.5 g (64%) of a white solid.

Provenance & Evidence