Hydrochloric Acid → HCID 178439742, compound

Participants

Reaction Steps

4-[2-(Tert-butoxycarbonyl)propenyl]-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.32 g) in methylene chloride (4 mL) was added to boron tribromide (0.33 mL) in methylene chloride (4 mL) at room temperature under argon. The mixture was stirred at room temperature for 1.5 hours and then it was added to saturated aqueous sodium bicarbonate (24 mL). The mixture was stirred for 10 minutes and then it was acidified to pH 5 with concentrated hydrochloric acid. The suspension was cooled to -10° C. and the solid was filtered off, washed with water, and vacuum dried to give a white solid (0.16 g). The solid was dissolved in hot methanol (60 mL), filtered, and concentrated to 10 mL volume. The suspension was cooled in an ice bath and the solid was filtered off, washed with cold methanol, and vacuum dried to give a white solid (0.1051 g); mp=242.2°-243.0° C. (dec); 1H NMR (d6 :DMSO) 7.48 (s,1) for olefin proton; MS: m/z=264, 290, 308 (M+1). Analysis for C14H10ClNO5 : Calculated: C, 54.65; H, 3.28; N, 4.55; Found: C, 54.85; H, 3.48; N, 4.50.

Provenance & Evidence