Selenium Dioxide → Ethyl 2-formylnicotinate

HRID 481105

Reaction equation

HRID 481105 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-formylnicotinateYield 40.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 11.3 g (0.069 mol) of 2-methyl-nicotinic acid ethyl ester and 8.4 g (0.076 mol) of selenium dioxide in 150 mL of dioxane is refluxed under nitrogen for 4 hours. The reaction mixture is cooled to room temperature and filtered. The filtrate is evaporated and the residue is chromatographed on 400 grams of silica gel using 50/50 ethyl acetate/hexanes as the eluant. Appropriate fractions are combined to yield 5 g of 2-formyl-nicotinic acid ethyl ester. 1H NMR (CDCl3) δ10.3 (s, 1H), 8.8 (m, 1H), 8.0 (m, 1H), 7.5 (m, 1H), 4.30 (q, 2H), 1.4 (t, 3H). TLC (7/3 hexanes/ethyl acetate) Rf=0.2.

Workup

  1. temperatureis refluxed under nitrogen for 4 hours
  2. filtrationfiltered
  3. customThe filtrate is evaporated
  4. customthe residue is chromatographed on 400 grams of silica gel using 50/50 ethyl acetate/hexanes as the eluant

Sources & evidence

ORD record
ord-f2df890f7e5a430293dff0426a156f13
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Linked notes

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