Pyrido[1,2-b]isoquinolin-5-ium perchlorate → HCID 22356189, compound

HRID 1780902Notes

Reaction equation

HRID 1780902 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH:6]1[C:15]2[CH:14]=[C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]3=[CH:11][N+:10]=2[CH:9]=[CH:8][CH:7]=1.COC1C=CC(CN2C=CC(C(C3C=CN(CC4C=CC(OC)=CC=4)N=3)=C)=N2)=CC=1>[N+](C)([O-])=O>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH:6]1[C:15]2[CH2:14][C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[CH2:11][N+:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 15186200Pyrido[1,2-b]isoquinolin-5-ium perchlorateHCID 19047580HCID 19047580, compound

Product 1

HCID 22356189HCID 22356189, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A reaction mixture containing benzo[b]quinolizinium perchlorate (9.5 g; 6.8 mmol) and 1,1-di-[(1-p-methoxybenzyl)-pyrazol-3-yl)ethylene (14.9 g; 0.034 mol) in 300 mL of nitromethane was refluxed for 16 h under nitrogen. The reaction mixture was concentrated in vacuo, the residue was triturated with 400 mL of methanol, and the solid was filtered, and dried (60° C.) to afford 22.1 g (85.6%) of 6,11-ethano-12,12-di-[(1-p-methoxybenzyl) pyrazol-3-yl)]-6,11-dihydrobenzo[b]quinolizinium perchlorate (Formula I: R1 =R2 =R3 =R4 =R7 =H ;R5 =R6 =1-p-methoxybenzyl-3-pyrazolyl;X- =ClO4-), as a solid.

Workup

  1. temperaturewas refluxed for 16 h under nitrogen
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was triturated with 400 mL of methanol
  4. filtrationthe solid was filtered
  5. customdried (60° C.)

Sources & evidence

ORD record
ord-7efa731e8f694dbfb068dab0ee90d921
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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