Selenium Dioxide → 3-Chloro-5-vinyl-2,3'-bipyridine-6'-carbaldehyde

HRID 2089118Notes

Reaction equation

HRID 2089118 reaction equation
[Cl:1][C:2]1[C:3]([C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[N:4][CH:5]=[C:6]([CH:8]=[CH2:9])[CH:7]=1.[Se](=O)=[O:18]>O1CCOCC1>[Cl:1][C:2]1[C:3]([C:10]2[CH:11]=[N:12][C:13]([CH:16]=[O:18])=[CH:14][CH:15]=2)=[N:4][CH:5]=[C:6]([CH:8]=[CH2:9])[CH:7]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 578257023-Chloro-6'-methyl-5-vinyl-2,3'-bipyridine

Product 1

HCID 578256943-Chloro-5-vinyl-2,3'-bipyridine-6'-carbaldehydeYield 75.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.0 g of 3-chloro-6′-methyl-5-vinyl-2,3′-bipyridine (14) (17.3 mmol) prepared in Example 10 was dissolved in 50 mL of 1,4-dioxane, and 5.8 g of selenium dioxide (52 mmol) was added thereto. The mixture was refluxed under heating and stirring for 18 hours, and cooled to room temperature. Then, the mixture was concentrated under reduced pressure, and dissolved in ethyl acetate to be washed with water. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent:ethyl acetate/hexane=1/4) to obtain 3.2 g of 3-chloro-5-vinyl-2,3′-bipyridine-6′-carbaldehyde (yield 75%).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating
  3. concentrationThen, the mixture was concentrated under reduced pressure
  4. dissolutiondissolved in ethyl acetate
  5. washto be washed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was separated by column chromatography (eluting solvent:ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-afd9a63ff83f4555b92079249007b757
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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