Hydrochloric Acid → 1-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Reaktionsgleichung
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:5])#[N:2].CO[CH:16]=[CH:17][C:18](=O)[CH3:19].N12CCN(CC1)CC2.CO/C=C/C(=O)C.Cl>COCCOCCO>[F:13][C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:3]([C:1]#[N:2])[C:4]2=[O:5])=[CH:12][CH:11]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
A solution of 2-cyano-N-(4-fluorophenyl)acetamide (15 g, 84.2 mmol), 4-methoxybut-3-en-2-one (12.6 g, 125.9 mmol) and 1,4-diazabicyclo[2.2.2]octane (9.4 g, 84.2 mmol) in 2-(2-methoxyethoxy)ethanol (150 mL) was stirred with heating at 120° C. for 5 hr. (3E)-4-Methoxybut-3-en-2-one (4.2 g, 41.9 mmol) and 1,4-diazabicyclo[2,2,2]octane (4.7 g, 41.9 mmol) were further added to the reaction mixture, and the mixture was stirred with heating at 120° C. for 1 hr. 2N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (6 g, 31%) as a pale-brown solid.
Aufarbeitung
- temperaturewith heating at 120° C. for 1 hr
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
- washThe obtained solid was washed with ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-6abd68b8f551418a9767a5734fd8a080
- Quelldatensatz
- uspto-grants-2013_05
- Patentnummer
- US08445509B2
Notizen zur Reaktion
Wird geladen…