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

HRID 249085Notes

Reaction equation

HRID 249085 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-6280a01d627046bcb93ec215fa814505
Source dataset
uspto-grants-1993_05
Patent number
US05212314

Reaction notes

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