Hydrochloric Acid → 4-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 42468

Reaktionsgleichung

Reaktionsgleichung von HRID 42468
CC([O-])(C)C.[K+].[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].[CH3:13][C:14](=O)[CH:15]=[CH:16][CH2:17][CH3:18].O=O.Cl>CS(C)=O.O>[CH2:17]([C:16]1[CH:15]=[C:14]([CH3:13])[NH:12][C:10](=[O:11])[C:9]=1[C:7]#[N:8])[CH3:18]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 977Oxygen2×HCID 7898CyanoacetamideHCID 12990Hexen-2-alHCID 23665647Potassium tert-butoxide2×

Produkt 1

HCID 156418004-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrileAusbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of t-BuOK (22.85 g, 204.08 mmol) and cyanoacetamide (18.8 g, 224.1 mmol) in DMSO (300 mL) was added hex-3-en-2-one (20 g, 204.08 mmol) under argon atmosphere at room temperature. The reaction mixture was then stirred at room temperature for 30 min and then added additional t-BuOK (68.5 g, 612.05 mmol) was added. Argon gas was displaced by oxygen gas and the mixture stirred for 48 hrs at room temperature in presence of oxygen. Reaction was monitored by TLC. The reaction mixture was cooled to 0° C. and diluted with water (100 mL) followed by 4 N HCl (120 mL). The mixture was stirred for 15 min and the resulting solid was filtered. The solid was washed with water (1 L) and dried to afford the title compound, 4-ethyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile (10.5 g, 31%), as an off white solid. 1H NMR (CDCl3, 400 MHz): δ ppm 1.148-1.185 (t, 3H, J=7.4 Hz), 2.237 (s, 3H), 2.557-2.614 (m, 2H), 6.211 (s, 1H), 12.330 (broad s, 1H). MS (ES) [M+H]+ 161.06.

Aufarbeitung

  1. additionwas added
  2. customReaction
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. stirringThe mixture was stirred for 15 min
  5. filtrationthe resulting solid was filtered
  6. washThe solid was washed with water (1 L)
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5337bd3dbb4b4fc08f61043b4f31a815
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536179B2

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