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

HRID 1109576Notes

Reaction equation

HRID 1109576 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-008429953c49453cbb0da42072e0d227
Source dataset
uspto-grants-1994_06
Patent number
US05321021

Reaction notes

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