Selenium Dioxide → 5-Cyano-6-formyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester

HRID 27760Notes

Reaction equation

HRID 27760 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:7][C:8]=1[CH3:9])#[N:2].[Se](=O)=[O:22]>CCOCC>[C:1]([C:3]1[CH:4]=[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:7][C:8]=1[CH:9]=[O:22])#[N:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 867372175-Cyano-6-methyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester

Product 1

HCID 867372165-Cyano-6-formyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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).

Workup

  1. distillationThe solvent is distilled off in vacuo
  2. customthe oily residue crystallized with diethyl ether

Sources & evidence

ORD record
ord-08848c8983c8401ca0f082b68172436a
Source dataset
uspto-grants-1980_09
Patent number
US04223142

Reaction notes

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