2-Acetylpyridine → 1-[2-Oxo-2-(pyridin-2-yl)ethyl]pyridin-1-ium bromide

HRID 399147Notes

Reaction equation

HRID 399147 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[Br:10]Br>>[Br-:10].[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:1](=[O:3])[CH2:2][N+:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:4]=1

Participants

3

Reactant 2

HCID 142862-AcetylpyridineHCID 24408Bromine

Product 1

HCID 211951501-[2-Oxo-2-(pyridin-2-yl)ethyl]pyridin-1-ium bromide

Procedure

2-Acetylpyridine (100 mmol) is treated with bromine (6.2 mL, 0.12 mol) at reflux in 200 mL of CHCl 3 for 45 min. The solution is cooled to room temperature then washed with dilute aqueous NaHCO3 /Na2S2 O3. The organic phase is dried over Na2SO4, filtered, and evaporated. The residue is dissolved in 200 mL of tetrahydrofuran (THF) and 30 mL of pyridine is added. The resulting solution is refluxed for 30 min. The mixture is cooled and filtered to give the desired product. The nuclear magnetic resonance (NMR) and infrared (IR) spectra are consistent with the assigned structure and the product is homogeneous by TLC.

Workup

  1. washthen washed with dilute aqueous NaHCO3 /Na2S2 O3
  2. dry with materialThe organic phase is dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe residue is dissolved in 200 mL of tetrahydrofuran (THF)
  6. addition30 mL of pyridine is added
  7. temperatureThe resulting solution is refluxed for 30 min
  8. temperatureThe mixture is cooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-4be7911a4beb45db90c09e943081ab88
Source dataset
uspto-grants-1998_10
Patent number
US05817774

Reaction notes

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