Reaction #56038

ord-08848c8983c8401ca0f082b68172436a

Reaction equation

CCOC(=O)c1cc(C#N)c(C)nc1N1CCCCC1
5-cyano-6-methyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester
O=[Se]=O
selenium dioxide
→
CCOC(=O)c1cc(C#N)c(C=O)nc1N1CCCCC1
5-Cyano-6-formyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester

Reactants

CCOC(=O)c1cc(C#N)c(C)nc1N1CCCCC1
5-cyano-6-methyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester
O=[Se]=O
selenium dioxide

Reagents

None

Solvents

CCOCC
ether

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.DISTILLATIONThe solvent is distilled off in vacuo
  2. 2
    Otherthe oily residue crystallized with diethyl ether

Procedure

27 g of 5-cyano-6-methyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester (0.1 mol) and 12.2 g selenium dioxide (0.11 mol) are refluxed together in diethyleneglycoldimethyl ether with stirring for 1.5 hours. The solvent is distilled off in vacuo and the oily residue crystallized with diethyl ether. Yield 19 g (66%); m.p. 62°-64° C. (ether).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04223142uspto-grants-1980_09