Ammonium formate → 3-(4-cyanophenyl)-2,6-dimethyl-4-(1H)-pyridone

HRID 1614779Notes

Reaction equation

HRID 1614779 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([CH3:24])=[N:11][C:12]([CH3:23])=[CH:13][C:14]=2[O:15]CC2C=CC=CC=2)=[CH:5][CH:4]=1)#[N:2].C([O-])=O.[NH4+]>[Pd].CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14](=[O:15])[CH:13]=[C:12]([CH3:23])[NH:11][C:10]=2[CH3:24])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 151714353-(4-Cyanophenyl)-2,6-dimethyl-4-(phenylmethoxy)pyridine

Product 1

HCID 151713203-(4-cyanophenyl)-2,6-dimethyl-4-(1H)-pyridoneYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of compound D (240 mg), ammonium formate (120 mg) and 10% palladium on charcoal catalyst (40 mg) in methanol (5 ml) was stirred for 2 hours. The catalyst was removed by filtration and the filtrate was concentrated. The residue was partitioned between dichloromethane (10 ml) and water (10 ml). The aqueous phase was separated and further extracted with dichloromethane (3×10 ml). The combined extracts were dried and the solvent was removed by evaporation. The residue was triturated with ether to give 3-(4-cyanophenyl)-2,6-dimethyl-4-(1H)-pyridone (E) (65 mg), as a non-crystalline solid; NMR (CDCl3): 2.1(s,3H), 2.25(s,3H), 6.2(s,1H), 7.4(d,2H), 7.7(d,2H), 11.2(br s, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between dichloromethane (10 ml) and water (10 ml)
  4. customThe aqueous phase was separated
  5. extractionfurther extracted with dichloromethane (3×10 ml)
  6. customThe combined extracts were dried
  7. customthe solvent was removed by evaporation
  8. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-22576a0e5e0d45cca98382cbc067a88f
Source dataset
uspto-grants-1993_03
Patent number
US05198439

Reaction notes

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