Bromide ion → Benzo(b)quinolizinium, bromide (1:1)

HRID 742440Notes

Reaction equation

HRID 742440 reaction equation
[Br-:1].O1CCO[CH:3]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N+:8]=1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Br-]>Br>[Br-:1].[CH:12]1[C:7]2[CH:3]=[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]3=[CH:13][N+:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 259Bromide ionHCID 190474902-(1,3-Dioxolan-2-yl)-1-benzylpyridinium bromide

Product 1

HCID 202130Benzo(b)quinolizinium, bromide (1:1)Yield 87.6%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 1526.8 g (4.74 mol) of 2-(1,3-dioxolan-2-yl)-1-benzylpyridinium bromide in 9 L of 48% HBr solution was heated on a steam-bath until the bromide dissolved. The mixture was heated (heating mantle) in vacuo (aspirator) to remove HBr solution. The dry residue was suspended in 800 mL of HBr solution, cooled, and 4 L of THF was slowly added. The reaction mixture was filtered to afford 1080 g (87%) of benzo[b]quinolizinium bromide as a green solid. Benzo[b]quinolizinium bromide (586 g) was dissolved in 2.4 L of hot water and filtered to remove an insoluble dark material. The filtrate was cooled in ice-water for 4 h, filtered, and the residue was washed with water, dried in vacuo at room temperature for 9 days to afford 508.8 g (86.8%) of benzo[b]quinolizinium bromide (Formula II: R1 =R2 =R7 =H; X- --=Br-).

Workup

  1. dissolutiondissolved
  2. temperatureThe mixture was heated
  3. temperature(heating mantle) in vacuo (aspirator)
  4. customto remove HBr solution
  5. temperaturecooled
  6. addition4 L of THF was slowly added
  7. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-afe20e25e1034cb1ac9d4549f061a65f
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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