Water → HCID 12687102, compound

Participants

Reaction Steps

500mg of 9-cyan0-4-fluoro-10,11-dihydrodibenzo[b,f]thiepin-11-one hydrazone was dissolved in 5ml of diethylene glycol and to this mixture was added 500mg of sodium hydroxide in 5ml of diethylene glycol. The reaction mixture was heated with stirring at 180°-200° C for 2 hours. After cooling, 30ml 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 80mg of 9-carboxy-4-hydroxy-10,11-dihydrodibenzo[b,f]thiepin having a melting point of 171°-173° C.

Provenance & Evidence