Pyridine → 1,2-Dihydro-5-[1-(Methoxyimino)ethyl]-6-Methyl-2-oxo-3-pyridinecarbonitrile

HRID 569572Notes

Reaction equation

HRID 569572 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:11])[NH:8][C:9]=1[CH3:10])(=O)[CH3:2].Cl.[CH3:13][O:14][NH2:15].[N:16]1C=CC=C[CH:17]=1>CCO>[CH3:13][O:14][N:15]=[C:1]([C:4]1[CH:5]=[C:6]([C:17]#[N:16])[C:7](=[O:11])[NH:8][C:9]=1[CH3:10])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 44217365-acetyl-6-methyl-2(1H)-pyridinone

Product 1

HCID 1363427801,2-Dihydro-5-[1-(Methoxyimino)ethyl]-6-Methyl-2-oxo-3-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-acetyl-6-methyl-2-(1H)pyridinone (1.76 g, 0.010 mol), methoxyamine hydrochloride (0.90 g, 0.107 mol) and pyridine (5.0 ml) were heated and stirred in EtOH (150 ml) at reflux. The initially heterogeneous mixture cleared as everything went into solution. At the end of 2 hours a solid precipitated. The reaction mixture was allowed to cool to room temperature and the solid was collected by filtration. Recrystallization (EtOH) gave 0.70 g (35%) m.pt. 275°-285° C.

Workup

  1. temperaturewere heated
  2. temperatureat reflux
  3. customAt the end of 2 hours a solid precipitated
  4. filtrationthe solid was collected by filtration
  5. customRecrystallization (EtOH)
  6. customgave 0.70 g (35%) m.pt. 275°-285° C.

Sources & evidence

ORD record
ord-525ef35c4f6b413ebbb3d3ee79c5ae84
Source dataset
uspto-grants-1988_03
Patent number
US04732982

Reaction notes

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