1,2-Dibromoethane → Methyl 2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Participants

Reaction Steps

To a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.26 g, 6.2 mmol) dissolved in acetonitrile (100 mL) was added 1,2-dibromoethane (5.3 mL, 62 mmol) and cesium carbonate (8.1 g, 24.8 mmol). The reaction mixture was stirred at rt for 1 d. The mixture was then concentrated, diluted with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes) to afford methyl 2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.0 g, 65%). LC-MS: (FA) ES+ 248.

Provenance & Evidence