Water → HCID 12687102, compound

Participants

Reaction Steps

500 mg of 9-cyano-4-fluoro-10,11-dihydrodibenzo[b,f]thiepin-11-one hydrazone was dissolved in 5 ml of diethylene glycol and to this mixture was added 500 mg of sodium hydroxide in 5 ml of diethylene glycol. The reaction mixture was heated with stirring at 180°-200° C. for 2 hours. After cooling, 30 ml of water was added to the mixture, which was extracted with benzene. The aqueous layer was acidified with conc. hydrochloric acid, extracted with ethyl acetate and the extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain glutinous residue, which was chromatographed over silica gel and eluted with benzene-ethyl acetate (1:1). Recrystallization from diluted methanol solution of the crude product obtained from a first fraction afforded 80 mg of 9-carboxy-4-hydroxy-10,11-dihydrodibenzo[b,f]thiepin having a melting point of 171°-173° C.

Provenance & Evidence