Piperidine → Nicotinonitrile, 1,2-dihydro-2-oxo-1,4,6-trimethyl-

HRID 259370Notes

Reaction equation

HRID 259370 reaction equation
[CH3:1][NH:2][C:3](=[O:7])[CH2:4][C:5]#[N:6].[CH3:8][C:9](=O)[CH2:10][C:11](=O)[CH3:12].N1CCCCC1>C(O)C>[CH3:1][N:2]1[C:9]([CH3:8])=[CH:10][C:11]([CH3:12])=[C:4]([C:5]#[N:6])[C:3]1=[O:7]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 31261AcetylacetoneHCID 806222-Cyano-N-methylacetamide

Product 1

HCID 46479Nicotinonitrile, 1,2-dihydro-2-oxo-1,4,6-trimethyl-Yield 77.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-methyl cyanoacetamide (113 g., 1.15 mole), 2,4-pentanedione (115 g., 1.15 mole), piperidine (11.5 ml.) and anhydrous ethanol (250 ml.) are refluxed with stirring for 3 hours. The mixture is allowed to stand overnight at room temperature and the white crystalline precipitate is collected by filtration to give 1-methyl-3-cyano-4,6-dimethylpyrid-2-one, 144 g. (77.4% yield), mp. 202°-205° C.

Workup

  1. waitto stand overnight at room temperature
  2. filtrationthe white crystalline precipitate is collected by filtration

Sources & evidence

ORD record
ord-6f6cf203fc6a4fd2aa967563c666adab
Source dataset
uspto-grants-1977_07
Patent number
US04038065

Reaction notes

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