Selenium Dioxide → 6-(2-Chlorophenyl)picolinaldehyde

HRID 2309731Notes

Reaction equation

HRID 2309731 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[CH:10][CH:9]=1.[Se](=O)=[O:16]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([CH:14]=[O:16])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 12380163HCID 12380163, compound

Product 1

HCID 123801676-(2-Chlorophenyl)picolinaldehydeYield 90.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.2 g of 6-(2-chlorophenyl)-2-methylpyridine was dissolved in 100 ml dioxane, 1.8 g of selenium dioxide (Aldrich, Gold Label) was added and the mixture was refluxed for 16 hours. The solution was decanted, fresh selenium dioxide (1.8 g) was added and refluxing was continued for a further 4 days. The solids were filtered and 250 ml ether was added. The organic solution was washed five times with 50 ml H2O, dried over magnesium sulfate. Evaporation afforded an oil which was filtered through silica gel eluting with 30% ether-hexane to afford 3.2 g of 6-(2-chlorophenyl)-2-pyridinecarboxaldehyde as a pale yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. customThe solution was decanted
  3. additionfresh selenium dioxide (1.8 g) was added
  4. temperaturerefluxing
  5. filtrationThe solids were filtered
  6. addition250 ml ether was added
  7. washThe organic solution was washed five times with 50 ml H2O
  8. dry with materialdried over magnesium sulfate
  9. customEvaporation
  10. customafforded an oil which
  11. filtrationwas filtered through silica gel eluting with 30% ether-hexane

Sources & evidence

ORD record
ord-d5edb02abf45450c871820abda935638
Source dataset
uspto-grants-1987_09
Patent number
US04696938

Reaction notes

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