1,2,3,4,6,7-hexahydro-4-oxo-3-phenyl-3,11b-epithio-11bH-benzo[a]quinolizine-1-carbonitrile → 6,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quinolizine-1-carbonitrile
Reaction equation
[O:1]=[C:2]1[C:11]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)S[C:8]3([CH:9]([C:19]#[N:20])[CH2:10]2)[N:3]1[CH2:4][CH2:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=13>C[O-].[Na+]>[O:1]=[C:2]1[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][C:9]([C:19]#[N:20])=[C:8]2[N:3]1[CH2:4][CH2:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=12Participants
3
Procedure
1.7 g of 1,2,3,4,6,7-hexahydro-4-oxo-3-phenyl-3,11b-epithio-11bH-benzo[a]quinolizine-1-carbonitrile were heated at reflux for 2 hours together with a sodium methylate solution (prepared from 156 mg of sodium in 40 ml of methanol). After cooling, the crystallized-out product was removed by filtration under suction and recrystallized from isopropanol. There was obtained pure 6,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quinolizine-1-carbonitrile of m.p. 204°-205°.