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

HRID 654375Notes

Reaction equation

HRID 654375 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-33132c1977384443aa8bfd267174e0fe
Source dataset
uspto-grants-1992_07
Patent number
US05130318

Reaction notes

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