9-Chloro-10-methoxybenzo[b]quinolizinium perchlorate → 6-Butylbenzo[b]quinolizinium perchlorate

HRID 742503Notes

Reaction equation

HRID 742503 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].Cl[C:7]1[CH:8]=[CH:9][C:10]2[C:11]([C:20]=1OC)=[CH:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N+:18]=1[CH:19]=2>Br>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH2:8]([C:19]1[N+:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:12]=[C:11]2[CH:20]=[CH:7][CH:8]=[CH:9][C:10]=12)[CH2:7][CH2:20][CH3:11]

Participants

3

Reactant 1

HCID 110461649-Chloro-10-methoxybenzo[b]quinolizinium perchlorate

Product 1

HCID 190474766-Butylbenzo[b]quinolizinium perchlorateYield 152.6%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A reaction mixture containing 9-chloro-10-methoxybenzo[b]quinolizinium perchlorate (5 g; 14.83 mmol) and 48% HBr (50 ml) was refluxed with stirring for 18 hours. The mixture was concentrated in vacuo, the residue was redissolved in water, filtered, and the filtrate was treated with a sodium perchlorate solution with stirring for 40 minutes. The solid was filtered and recrystallized from acetone/ether (1:1) to afford 3.8 g (79%) of 9-chloro-10-hydroxy-benzo[b]quinolizinium perchlorate (Formula II: R1 =R2 =H; R7 =9--Cl; 10--OH; X- =CIO4-), m.p. 203°-205° C.

Workup

  1. temperaturewas refluxed
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue was redissolved in water
  4. filtrationfiltered
  5. additionthe filtrate was treated with a sodium perchlorate solution
  6. stirringwith stirring for 40 minutes
  7. filtrationThe solid was filtered
  8. customrecrystallized from acetone/ether (1:1)

Sources & evidence

ORD record
ord-a617e6935fe74a4f8273e17daf694924
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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