Water → 2-Methylpyridine-3-carbonitrile

HRID 52365

Reaktionsgleichung

Reaktionsgleichung von HRID 52365
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C(Cl)Cl>[C:4]([C:3]1[C:2]([CH3:1])=[N:10][CH:9]=[CH:8][CH:7]=1)#[N:6]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 122437052-Methylnicotinamide

Produkt 1

HCID 47383082-Methylpyridine-3-carbonitrileAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-methylnicotinamide from step 1 (11.1 g, 0.081 mol) in triethylamine (24.8 g, 0.243 mol) and 400 mL of methylene chloride was added trifluoroacetic anhydride (21.0 g, 0.100 mol) rapidly at 0° C. The reaction was complete after a few minutes at this temperature. Water was added and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with water, brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1) to give 7.2 g of 3-cyano-2methylpyridine as a pale yellow solid (75%): mp(DSC) 56°-58° C.

Aufarbeitung

  1. waitThe reaction was complete after a few minutes at this temperature
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe residue was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-9673fb8c9ca943f59b6b5e1aa4a9ca27
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616601

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