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

HRID 2249237Notes

Reaction equation

HRID 2249237 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-6methyl-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-b4d3fcf08cad4c27864b3f2a5f15dce3
Source dataset
uspto-grants-1991_08
Patent number
US05043449

Reaction notes

Loading…