Selenium Dioxide → Ethyl 2-formylnicotinate

HRID 1378918Notes

Reaction equation

HRID 1378918 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[CH3:11])[CH3:2].[Se](=O)=[O:14]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[CH:11]=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 74401Ethyl 2-methylnicotinate

Product 1

HCID 15639417Ethyl 2-formylnicotinate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

16.9 g of 2-methylnicotinic acid ethyl ester, 22.9 g of selenium (IV) oxide and 240 ml dioxane are combined and refluxed overnight under nitrogen. The mixture is cooled to RT, filtered Through celite, and evaporated. The resulting red sludge is diluted with ethylacetate, filtered twice through celite and the solvent removed by evaporation under vacuum.

Workup

  1. temperaturerefluxed overnight under nitrogen
  2. filtrationfiltered Through celite
  3. customevaporated
  4. additionThe resulting red sludge is diluted with ethylacetate
  5. filtrationfiltered twice through celite
  6. customthe solvent removed by evaporation under vacuum

Sources & evidence

ORD record
ord-7c43b47781964e58b572aa6e0618f25c
Source dataset
uspto-grants-1997_09
Patent number
US05670456

Reaction notes

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