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

HRID 648534Notes

Reaction equation

HRID 648534 reaction equation
[OH-].[OH:2][C:3]1[N+:7]2[CH2:8][CH2:9][C:10]3[C:15]([C:6]=2[S:5][C:4]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3.[C:22](#[N:25])[CH:23]=[CH2:24]>C1(C)C=CC=CC=1>[O:2]=[C:3]1[C:4]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:5][C:6]3([CH:23]([C:22]#[N:25])[CH2:24]2)[N:7]1[CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=13

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 190204015,6-Dihydro-3-hydroxy-2-phenylthiazolo-[2,3-a]isoquinolinium hydroxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.08 g of 5,6-dihydro-3-hydroxy-2-phenylthiazolo[2,3-a]isoquinolinium hydroxide (internal salt) and 1.95 ml of acrylonitrile were heated together under reflux overnight in 250 ml of toluene. After evaporation of the solvent in vacuo, the residue was recrystallized from acetonitrile. There was obtained 1,2,3,4,6,7-hexahydro-4-oxo-3-phenyl-3,11b-epithio-11bH-benzo[a]quinolizine-1-carbonitrile of m.p. 225°-226°.

Workup

  1. customAfter evaporation of the solvent in vacuo
  2. customthe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-cc187d30e2eb40f4a200bfea9da46392
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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