Hydrochloric Acid → 1-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-ethanone

Participants

Reaction Conditions

Reaction Steps

1-(5-Chloro-1H,3H-benzo[de]isochromen-6-yl)-ethylidene-amine (22 g) obtained in Step 1 described above was dissolved in tetrahydrofuran (200 mL), 5 N aqueous hydrochloric acid solution (200 mL) was added, and this was stirred while heating at 80° C. for 48 hours. After cooling the mixture to room temperature, the solvent was removed by using a rotary evaporator. The obtained residue was dissolved in ethyl acetate (400 mL), then washed with water (300 mL) and saturated sodium hydrogen carbonate solution successively, and then dried over sodium sulfate. A residue obtained after filtration and concentration was purified by silica gel column chromatography (developing solvent; n-hexane:dichloromethane:ethyl acetate=10:10:1), and thus, 1-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-ethanone (19.2 g) was obtained as a white solid.

Provenance & Evidence