Hydrochloric Acid → Methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(1,3-dioxolan-2-ylmethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.23 g, 0.8 mmol) in tetrahydrofuran (5 mL) was added 1.0 M hydrochloric acid in water (9.0 mL). The reaction mixture was heated to 65° C. and stirred overnight. The mixture was cooled to rt, water was added and the mixture was extracted with DCM (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 (30% to 100% EtOAc/hexanes) to afford methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylate (0.11 g, 56%). LC-MS: (FA) ES+ 246.

Provenance & Evidence