HCID 19864646, compound → HCID 19864641, compound

Participants

Reaction Steps

10,11-Dihydro-10-hydroxy-dibenz[b,f]oxepine-10-methanamine (46.6 g - as prepared in example A) was dissolved in a mixture of water (940 ml) and acetic acid (23 ml), and the solution was filtered and cooled below 5° C. To this cooled solution was quickly added a solution of sodium nitrite (20.5 g) in the minimum of water, the cooling was then removed, and the mixture was allowed to stand at ambient temperature for eighteen hours. The product was filtered, dissolved in dichloromethane, and the solution was filtered through silica, then evaporated. The residue was crystallised from 1,1'-oxybisethane/n-hexane to give pure 5H-dibenz[b,g]oxocin-6(7H)-one (34 g). M.P. 86° C. (Lit. 84.5° C. J.Org.Chem.34.1165(1969).

Provenance & Evidence