Selenium Dioxide → Ethyl 2-formylnicotinate

HRID 2372201Notes

Reaction equation

HRID 2372201 reaction equation
[CH3:1][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Se](=O)=[O:14]>O1CCOCC1>[CH:1]([C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:14]

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

A solution of ethyl 2-methylnicotinate (2.0 g, 12.12 mmol), selenium dioxide (20.0 g, 18.18 mmol) and dioxane (10 ml) is heated at 135° for 4 hours. The reaction mixture is filtered and the filtrate is concentrated and purified by prep. TLC to give ethyl 2-formylnicotinate.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. custompurified by prep

Sources & evidence

ORD record
ord-d7a2e87fc5b5468aabf7f1fa901ffd6a
Source dataset
uspto-grants-1992_03
Patent number
US05098466

Reaction notes

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