Hydrochloric Acid → 2-Methylpyridine-4-carbonitrile

HRID 1497272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497272
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[CH3:10][Al](C)C.Cl>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 5686382-Chloro-4-cyanopyridineHCID 16682925Trimethylaluminum

Produkt 1

HCID 119590732-Methylpyridine-4-carbonitrileAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 2-chloroisonicotinonitrile (2 g, 14.4 mmol), trimethylaluminum (7.94 ml, 15.9 mmol) and tetrakis(triphenylphosphine)palladium (0) (367 mg, 318 μmol) in dioxane (20.0 ml) was heated to reflux for 4 h. The reaction mixture was poured on 1N HCl and extracted two times with EtOAc. The aqueous layer was basified with 3N NaOH and extracted with EtOAc. The combined organic extracts were dried with Na2SO4 and evaporated. The remaining solid was purified by column chromatography (silica gel, dichloromethane/EtOAc 95:5) to afford the title compound (980 mg, 57%) as white solid. 1H NMR (CDCl3, 300 MHz): 2.64 (s, 3H), 7.34 (d, J=5.05 Hz 1H), 7.40 (s, 1H), 8.68 (d, J=5.05 Hz, 1H).

Aufarbeitung

  1. temperatureto reflux for 4 h
  2. extractionextracted two times with EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried with Na2SO4
  5. customevaporated
  6. customThe remaining solid was purified by column chromatography (silica gel, dichloromethane/EtOAc 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-9e76c94f427b412781233da037c20c9b
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199938B2

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