6-Methyl-5-phenyl-3,4-dihydropyridin-2(1H)-one → 6-Methyl-5-phenylpyridin-2(1H)-one

HRID 1995617Notes

Reaction equation

HRID 1995617 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CC1C=CC(C(C)C)=CC=1.[Pd]>[CH3:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 135028526-Methyl-5-phenyl-3,4-dihydropyridin-2(1H)-one

Product 1

HCID 135028506-Methyl-5-phenylpyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7463P-CymeneSolvent

Procedure

3,4-Dihydro-6-methyl-5-phenyl-2(1H)-pyridone (25.6 grams) and 5% palladium/on carbon (4.9 grams) were refluxed for about 18 hours in 750 ml p-cymene. Since little product formed upon cooling, the reaction mixture was boiled and distilled until a constant temperature of 173° C. was reached. Refluxing continued for 36 hours and then the reaction mixture was filtered hot. Upon cooling, a solid precipitate formed which was collected and washed with ether, yield 13.0 grams, m.p. 201°-208° C.

Workup

  1. customSince little product formed
  2. temperatureupon cooling
  3. distillationdistilled until a constant temperature of 173° C.
  4. temperatureRefluxing
  5. filtrationthe reaction mixture was filtered hot
  6. temperatureUpon cooling
  7. customa solid precipitate formed which
  8. customwas collected
  9. washwashed with ether, yield 13.0 grams, m.p. 201°-208° C.

Sources & evidence

ORD record
ord-c74f40ff78f540e593ec41598dc2bd76
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Reaction notes

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