Ethyl isonicotinate → 2-Cyano-2-[4-(1,1-dimethylethyl)phenyl]-1-(4-pyridyl)ethanone

HRID 1167652Notes

Reaction equation

HRID 1167652 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:12][C:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1)([CH3:15])[CH3:14].CC(C)([O-])C.[K+]>C(O)(C)(C)C.O>[C:23]([CH:22]([C:19]1[CH:20]=[CH:21][C:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[CH:17][CH:18]=1)[C:1]([C:2]1[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=1)=[O:9])#[N:24]

Participants

6

Reactant 3

HCID 15291Ethyl isonicotinateHCID 76784(4-tert-Butylphenyl)acetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 229937442-Cyano-2-[4-(1,1-dimethylethyl)phenyl]-1-(4-pyridyl)ethanoneYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl isonicotinate (12 g) and 4-(1,1-Dimethylethyl)phenylacetonitrile (9.1 g) in tert-butyl alcohol (36 mL), was added potassium tert-butoxide (7.3 g), and the mixture was stirred at 100° C. for 3 h. After cooling, the resulting mixture was dissolved in water and washed with isopropyl ether. The aqueous phase was adjusted to pH 7.0 with 2 N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried, and the solvent was evaporated. The crystalline residue was recrystallized from ethyl acetate-isopropyl ether to obtain 2-cyano-2-[4-(1,1-dimethylethyl)phenyl]-1-(4-pyridyl)ethanone (5.09 g, yield 35%).

Workup

  1. temperatureAfter cooling
  2. washwashed with isopropyl ether
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was evaporated
  7. customThe crystalline residue was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-c388df1a2ee94b51a832892f3e659873
Source dataset
uspto-grants-2003_09
Patent number
US06620825B1

Reaction notes

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