Selenium Dioxide → 6-(2,4-Dichlorophenyl)-2-pyridinecarboxaldehyde

HRID 2309741Notes

Reaction equation

HRID 2309741 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([CH3:15])[CH:12]=[CH:11][CH:10]=1.[Se](=O)=[O:17]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([CH:15]=[O:17])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24007Selenium Dioxide2×HCID 212757502-(2,4-Dichlorophenyl)-6-methylpyridine

Product 1

HCID 201846896-(2,4-Dichlorophenyl)-2-pyridinecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.5 g of 6-(2,4-dichlorophenyl)-2-methylpyridine was dissolved in 200 ml of 1,4-dioxane and treated with 1.05 g of selenium dioxide (Aldrich, Gold Label). The mixture was refluxed for 72 hours. An additional 1.2 g of selenium dioxide was added and the mixture was heated a further 48 hours. The solids were removed by filtration and the dioxane was evaporated to afford crude 6-(2,4-dichlorophenyl)-2-pyridinecarboxaldehyde which was chromatographed on silica-gel to afford 1.5 g of 6-(2,4-dichlorophenyl)-2-pyridinecarboxaldehyde as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 72 hours
  2. temperaturethe mixture was heated a further 48 hours
  3. customThe solids were removed by filtration
  4. customthe dioxane was evaporated

Sources & evidence

ORD record
ord-97b2acdb06c14d1f9d8f1235e796b23f
Source dataset
uspto-grants-1987_09
Patent number
US04696938

Reaction notes

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