Methane → 9-Fluoropyrido[1,2-b]isoquinolin-5-ium perchlorate

HRID 1647714Notes

Reaction equation

HRID 1647714 reaction equation
[Br-].[F:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N+:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]2OCCO2)=[CH:5][CH:4]=1.C.[Cl:22]([O-:26])(=[O:25])(=[O:24])=[O:23].[Na+]>CS(O)(=O)=O>[Cl:22]([O-:26])(=[O:25])(=[O:24])=[O:23].[F:2][C:3]1[CH:4]=[CH:5][C:6]2[C:19]([CH:20]=1)=[CH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][N+:8]=1[CH:7]=2

Participants

5

Reactant 3

HCID 297MethaneHCID 522606Sodium PerchlorateHCID 19047513HCID 19047513, compound

Product 1

HCID 190475259-Fluoropyrido[1,2-b]isoquinolin-5-ium perchlorateYield 59%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
105 °C

Procedure

1-(4-Fluorobenzyl)-2-(1,3-dioxolan-2-yl)pyridinium bromide (31 g, 0. 091 mol) was added to a mixture of polyphosphoric acid (350 g) and methanesulfonic acid (100 mL) at 40° C. and the resulting mixture was heated at 105° C. for 2 hours. The mixture was poured onto ice and the solution was treated with charcoal. The mixture was added to an excess of sodium perchlorate and the solution was chilled and allowed to stand for 16 hours. A precipitate formed, which was collected by filtration to afford 15.9 g (59%) of 9-fluorobenzo[b]quinolizinium perchlorate (Formula VII: R2 =9--F; R3 =R4 =H; X- =ClO4-), as a yellow solid, m.p. 168°-173° C.

Workup

  1. additionThe mixture was poured onto ice
  2. temperaturethe solution was chilled
  3. customA precipitate formed
  4. filtrationwhich was collected by filtration

Sources & evidence

ORD record
ord-b8a3e87671cf422499de5695b519a3b7
Source dataset
uspto-grants-1995_07
Patent number
US05434159

Reaction notes

Loading…