Selenium Dioxide → 5-Cyano-6-formyl-2-[(1-methylpropyl)amino]-3-pyridine-carboxylic acid, ethyl ester

HRID 27763Notes

Reaction equation

HRID 27763 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]([NH:10][CH:11]([CH3:14])[CH2:12][CH3:13])=[N:7][C:8]=1[CH3:9])#[N:2].[Se](=O)=[O:21]>O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]([NH:10][CH:11]([CH3:14])[CH2:12][CH3:13])=[N:7][C:8]=1[CH:9]=[O:21])#[N:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 867372195-Cyano-6-methyl-2-[(1-methylpropyl)amino]-3-pyridine-carboxylic acid, ethyl ester

Product 1

HCID 867372205-Cyano-6-formyl-2-[(1-methylpropyl)amino]-3-pyridine-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

26.1 g of 5-cyano-6-methyl-2-[(1-methylpropyl)amino]-3-pyridine-carboxylic acid, ethyl ester (0.1 mol) and 13 g of selenium dioxide are refluxed together in dioxane for 24 hours. After this time the selenium is filtered off and the solvent removed in vacuo. The resulting oily residue is crystallized with ether. Yield 19 g (69%); m.p. 37°-38° C. (methanol).

Workup

  1. filtrationAfter this time the selenium is filtered off
  2. customthe solvent removed in vacuo
  3. customThe resulting oily residue is crystallized with ether

Sources & evidence

ORD record
ord-2262b51bdca24ee2979efa35425d1902
Source dataset
uspto-grants-1980_09
Patent number
US04223142

Reaction notes

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