p-Toluenesulfonic acid → HCID 10465943, compound

Participants

Reaction Steps

16.7 g of 6-fluoro-3,4-dihydro-2(1H)-naphthalenone in 200 ml of benzene are boiled at reflux for 2.5 hours with 8.4 ml of pyrrolidine and 0.35 g of anhydrous p-toluenesulfonic acid. The 1-(6-fluoro-3,4-dihydro-2-naphthyl)pyrrolidine obtained is treated, without purification, with 10.8 g of acrylamide and 0.5 g of p-toluenesulfonic acid. The mixture is heated under nitrogen at 100° for 2 hours and at 150° for 2 hours. The mixture is dissolved in 180 ml of chloroform, washed with water and chromatographed over 150 g of silica gel with chloroform. Recrystallization from ethyl acetate gives 8-fluoro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one with melting point 223°-224°.

Provenance & Evidence