HCID 13565732, compound → HCID 21779936, compound

HRID 622095Notes

Reaction equation

HRID 622095 reaction equation
[C:1]([C:9]1[CH:10]=[C:11](C#N)[C:12](=[O:16])[NH:13][C:14]=1[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[C:1]([C:9]1[CH:10]=[CH:11][C:12](=[O:16])[NH:13][C:14]=1[CH3:15])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 13565732HCID 13565732, compound

Product 1

HCID 21779936HCID 21779936, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-Benzoyl-1,2-dihydro-6-methyl-2-oxo-3-pyridine-carbonitrile (2.32 g, 0.013 mole) and concentrated HCl (50 ml) are heated and stirred at reflux under an argon atmosphere for 5 hours. Upon cooling to room temperature a solid precipitates. The solid is collected by filtration and allowed to air dry. The dry solid is heated to 280°-290° C. and maintained at this temperature for 7 minutes. The residue is 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) gives the title compound.

Workup

  1. temperatureat reflux under an argon atmosphere for 5 hours
  2. customprecipitates
  3. filtrationThe solid is collected by filtration
  4. customto air dry
  5. temperatureThe dry solid is 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

Sources & evidence

ORD record
ord-7d089f393de04a368d827362d207165b
Source dataset
uspto-grants-1988_09
Patent number
US04769380

Reaction notes

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