Pyridine → 6-Isobutyl-5-methylnicotinonitrile

HRID 2065894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2065894
[CH2:1]([C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9]([NH2:11])=O)=[CH:7][N:6]=1)[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9]#[N:11])=[CH:7][N:6]=1)[CH:2]([CH3:4])[CH3:3]

Komponenten

4

Edukt 2

HCID 1049PyridineHCID 670268976-Isobutyl-5-methylnicotinamide

Produkt 1

HCID 670269756-Isobutyl-5-methylnicotinonitrileAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 6-isobutyl-5-methyl-nicotinamide (1.89 g, 9.85 mmol) in DCM (40 mL) and pyridine (2.83 g, 39.4 mmol), TFA anhydride (5.17 g, 24.6 mmol) is added portionwise at 0° C. The mixture is stirred at rt for 24 h, diluted with DCM and washed with water, 4% aq. citric acid solution followed by sat. aq. NaHCO3 solution. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 6-isobutyl-5-methyl-nicotinonitrile (1.35 g) as a white solid; LC-MS: tR=0.89 min, [M+1]+=175.11.

Aufarbeitung

  1. washwashed with water, 4% aq. citric acid solution
  2. extractionextract
  3. dry with materialis dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Quellen und Nachweise

ORD-Eintrag
ord-ed548ffc34534ec9930bf45ed8a362cf
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288554B2

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