Pyridine → HCID 15818071, compound

HRID 399148Notes

Reaction equation

HRID 399148 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[N:5]=1)(=[O:3])[CH3:2].BrBr.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl.O1CCCC1>[Br-:10].[Br:10][C:6]1[N:5]=[C:4]([C:1](=[O:3])[CH2:2][N+:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 15818071HCID 15818071, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Acetyl-6-bromopyridine from example 1 (20.0 g, 100 mmol) was treated with bromine (6.2 mL, 0.12 mol) at reflux in 200 mL of CHCl3 for 45 min. The solution was cooled to room temperature then washed with dilute aqueous NaHCO3 /Na2S2O3. The organic phase was dried over Na2SO4, filtered, and evaporated to give an oil. The oil was dissolved in 200 mL of tetrahydrofuran (THF) and 30 mL of pyridine was added. The resulting solution was refluxed for 30 min. The mixture was cooled and filtered to give 26.1 g of off-white powder (73% yield); mp 256° C. (decomposition; discolors at 245° C.). The nuclear magnetic resonance (NMR) and infrared (IR) spectra were consistent with the assigned structure and the product was homogeneous by TLC.

Workup

  1. washthen washed with dilute aqueous NaHCO3 /Na2S2O3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil
  6. temperatureThe resulting solution was refluxed for 30 min
  7. temperatureThe mixture was cooled
  8. filtrationfiltered

Sources & evidence

ORD record
ord-9868080d27434fae8587518989c3510b
Source dataset
uspto-grants-1998_10
Patent number
US05817774

Reaction notes

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