Reaktion #307960

Reaktionsgleichung

1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-benzo[b]azepin-5-one

NaOH

→

title compound

Ausbeute 79.0%

1,2,3,4-Tetrahydro-benzo[b]azepin-5-one

Ausbeute 79.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONIt was poured into ice
2. 2
   ExtraktionThe aqueous layer was extracted twice with dichloromethane
3. 3
   Waschenwashed with brine
4. 4
   Sonstigedried
5. 5
   SonstigeThe residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane)

Vorschrift

Polyphosphoric acid (25 g) was heated at 100° C. under nitrogen until it could be stirred. 1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-benzo[b]azepin-5-one from Example E5.4 (2.6 g, 8.26 mmol) was added portionwise and the reaction mixture was heated at 100° C. for 1.5 h. It was poured into ice and basified with 2M NaOH(aq). The aqueous layer was extracted twice with dichloromethane. The organic extracts were combined, washed with brine, dried and reduced in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane) to yield the title compound (1.05 g, 79%).

Quelle