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

HRID 231879Notes

Reaction equation

HRID 231879 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-311d57fa1c104a988f23843c7b60d96d
Source dataset
uspto-grants-1989_07
Patent number
US04849522

Reaction notes

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