Acetone → HCID 55263195, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared according to the procedure of Pelcman (W02006032851, 1996). A 250 mL flask, equipped with a magnetic stirbar and reflux condenser, was charged with 3′-nitro-7′,8′-dihydro-5′H-spiro[1,3-dioxolane-2,6′-quinoline] (4.75 g, 20.1 mmol), acetone (65 mL), hydrochloric acid (2N (aq), 42 mL), and water (21 mL). The mixture was heated to 65° C. for 1 h, then to 80° C. for 30 minutes. The mixture was cooled to ambient temperature and neutralized with saturated NaHCO3 (aq) until pH=8. The mixture was extracted with EtOAc (3×) and the combined organic portions were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (30 to 60% EtOAc in hexanes) to afford the title compound (2.5 g, 65%).

Provenance & Evidence