2,3-Lutidine → 3-Methylpyridine-2-carboxaldehyde

HRID 1796758Notes

Reaction equation

HRID 1796758 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[C:2]=1[CH3:8].[Se](=O)=[O:10]>O1CCOCC1>[CH3:7][C:3]1[C:2]([CH:8]=[O:10])=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 114202,3-LutidineHCID 24007Selenium Dioxide

Product 1

HCID 15018743-Methylpyridine-2-carboxaldehydeYield 37.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,3-Lutidine (1.0 g, 9.33 mmol) was refluxed in a 1,4-dioxane (20 ml) solution in the presence of selenium dioxide (1.24 g, 11.2 mmol) in an argon atmosphere for one hr. The temperature of the reaction solution was then returned to room temperature, and the reaction solution was filtered. The solvent was removed from the filtrate by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:2) to give 422 mg (37.3%) of 3-methylpyridine-2-carbaldehyde as a colorless liquid.

Workup

  1. customwas then returned to room temperature
  2. filtrationthe reaction solution was filtered
  3. customThe solvent was removed from the filtrate by distillation under the reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:2)

Sources & evidence

ORD record
ord-d908f53c389940849b658b454f45fe22
Source dataset
uspto-grants-2006_04
Patent number
US07030120B2

Reaction notes

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