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

HRID 1067883Notes

Reaction equation

HRID 1067883 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>C(Cl)(Cl)Cl>[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

4

Reactant 2

HCID 142862-AcetylpyridineHCID 24408Bromine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Acetylpyridine (100 mmol) is treated with bromine (6.2 mL, 0.12 mol) at reflux in 200 mL of CHCl3 for 45 min. The solution is cooled to room temperature then washed with dilute aqueous NaHCO3/Na2S2O3. 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/Na2S2O3
  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-3a55bb01c2224cbaa7380eefb79e929a
Source dataset
uspto-grants-2001_06
Patent number
US06248870B1

Reaction notes

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