Selenium Dioxide → 2-Butylamino-5-cyano-6-formyl-3-pyridine-carboxylic acid, ethyl ester

HRID 27756Notes

Reaction equation

HRID 27756 reaction equation
[CH2:1]([NH:5][C:6]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]([C:17]#[N:18])=[C:8]([CH3:19])[N:7]=1)[CH2:2][CH2:3][CH3:4].[Se](=O)=[O:21]>CCOCC>[CH2:1]([NH:5][C:6]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]([C:17]#[N:18])=[C:8]([CH:19]=[O:21])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 867372122-Butylamino-5-cyano-6-methyl-3-pyridine-carboxylic acid, ethyl ester

Product 1

HCID 867372132-Butylamino-5-cyano-6-formyl-3-pyridine-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

130.5 g of 2-butylamino-5-cyano-6-methyl-3-pyridine-carboxylic acid, ethyl ester (0.5 mol) are dissolved in 400 ml of diethyleneglycoldimethyl ether. 61.1 g of selenium dioxide are added and the mistrue is heated at reflux temperature for 1 hour. The mixture is filtered hot and evaporated to dryness. The resulting yellow oil of 2-butylamino-5-cyano-6-formyl-3-pyridine-carboxylic acid, ethyl ester is crystallized with diethyl ether. Yield 95 g (69%); m.p. 81°-83° C. (methanol).

Workup

  1. temperaturethe mistrue is heated
  2. temperatureat reflux temperature for 1 hour
  3. filtrationThe mixture is filtered hot
  4. customevaporated to dryness
  5. customThe resulting yellow oil of 2-butylamino-5-cyano-6-formyl-3-pyridine-carboxylic acid, ethyl ester is crystallized with diethyl ether

Sources & evidence

ORD record
ord-1d20e3ec177542ccb7e74defae82fc17
Source dataset
uspto-grants-1980_09
Patent number
US04223142

Reaction notes

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