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

HRID 27759Notes

Reaction equation

HRID 27759 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[N:7][C:8]=1[CH3:9])#[N:2].[Se](=O)=[O:27]>CCOCC>[C:1]([C:3]1[CH:4]=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)=[N:7][C:8]=1[CH:9]=[O:27])#[N:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 131711880HCID 131711880, compound

Product 1

HCID 1317118825-Cyano-6-formyl-2-[[3-(trifluormethyl)phenyl]amino]-3-pyridine-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

69.8 g of 5-cyano-6-methyl-2-[[3-(trifluormethyl)phenyl]amino]-3-pyridine-carboxylic acid, ethyl ester (0.2 mol) are dissolved in 400 ml of diethyleneglycoldimethyl ether. After addition of 24.2 g of selenium dioxide, the mixture is heated at 160° with stirring for 2 hrs. The selenium is filtered off and the filtrate evaporated. The resulting yellow title compound is recrystallized from butanol. Yield 56 g (77%); m.p. 183°-185° C.

Workup

  1. temperaturethe mixture is heated at 160°
  2. filtrationThe selenium is filtered off
  3. customthe filtrate evaporated
  4. customThe resulting yellow title compound is recrystallized from butanol

Sources & evidence

ORD record
ord-8e2406209b18496587e959bf85c5e589
Source dataset
uspto-grants-1980_09
Patent number
US04223142

Reaction notes

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