Reaktion #1287291

Reaktionsgleichung

10,11-Dihydro-10-hydroxy-dibenz[b,f]oxepine-10-methanamine

→

5H-dibenz[b,g]oxocin-6(7H)-one

Ausbeute 78.5%

Lösungsmittel

water

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe solution was filtered
2. 2
   Temperaturcooled below 5° C
3. 3
   workup.ADDITIONTo this cooled solution was quickly added a solution of sodium nitrite (20.5 g) in the minimum of water
4. 4
   Sonstigethe cooling was then removed
5. 5
   workup.WAITto stand at ambient temperature for eighteen hours
6. 6
   FiltrationThe product was filtered
7. 7
   workup.DISSOLUTIONdissolved in dichloromethane
8. 8
   Filtrationthe solution was filtered through silica
9. 9
   Sonstigeevaporated
10. 10
    SonstigeThe residue was crystallised from 1,1'-oxybisethane/n-hexane

Vorschrift

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).

Quelle