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

HRID 477929Notes

Reaction equation

HRID 477929 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]=12

Participants

3

Reactant 1

HCID 190204021,2,3,4,6,7-hexahydro-4-oxo-3-phenyl-3,11b-epithio-11bH-benzo[a]quinolizine-1-carbonitrile

Product 1

HCID 190203806,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quinolizine-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

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°.

Workup

  1. temperatureAfter cooling
  2. customthe crystallized-out product was removed by filtration under suction
  3. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-22921527b9cf47189c7c8fb662699915
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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