5-Acetyl-2-hydroxy-6-methylnicotinonitrile → 5-acetyl-6-methyl-2(1H)-pyridinone

HRID 2249235Notes

Reaction equation

HRID 2249235 reaction equation
[C:1]([C:4]1[CH:5]=[C:6](C#N)[C:7](=[O:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2]>Cl>[C:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 27654765-Acetyl-2-hydroxy-6-methylnicotinonitrile

Product 1

HCID 44217365-acetyl-6-methyl-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile (2.32 g, 0.013 mole) and concentrated HCl (50 ml) were heated and stirred at reflux under an argon atmosphere for 5 hours. Upon cooling to room temperature a solid precipitated. The solid was collected by filtration and allowed to air dry. The dry solid (1.25 g) was heated to 280°-290° C. and maintained at this temperature for 7 minutes. The residue was allowed to cool to room temperature then extracted into methylene chloride. Concentration of the methylene chloride solution followed by flash chromatography (50% methylene chloride-ethyl acetate) gave 0.46 g m.pt. 201°-202° C. (1:t 196°-198° C.).

Workup

  1. temperatureat reflux under an argon atmosphere for 5 hours
  2. customprecipitated
  3. filtrationThe solid was collected by filtration
  4. customto air dry
  5. temperatureThe dry solid (1.25 g) was heated to 280°-290° C.
  6. temperaturemaintained at this temperature for 7 minutes
  7. temperatureto cool to room temperature
  8. extractionthen extracted into methylene chloride
  9. customgave 0.46 g m.pt. 201°-202° C. (1:t 196°-198° C.)

Sources & evidence

ORD record
ord-d0af7b1317f24e2aad763defea981b01
Source dataset
uspto-grants-1991_08
Patent number
US05043449

Reaction notes

Loading…