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

HRID 2304604

Reaktionsgleichung

[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]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

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%).

Aufarbeitung

temperatureAfter cooling
washwashed with isopropyl ether
extractionextracted with ethyl acetate
washThe extract was washed with water
customdried
customthe solvent was evaporated
customThe crystalline residue was recrystallized from ethyl acetate-isopropyl ether

Quellen und Nachweise

ORD-Eintrag: ord-603c61fb75154f07ba90e9b15f3dfddd
Quelldatensatz: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06436966B1

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