Water → 5-Methylnicotinonitrile

HRID 1166373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166373
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](C(N)=O)=[N:6][CH:7]=1.[CH2:11]([N:13](CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C(Cl)Cl>[C:11]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)#[N:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 123629375-Methylpyridine-2-carboxamide

Produkt 1

HCID 6378385-MethylnicotinonitrileAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 5-methylpyridinylcarboxamide from step 2 (10.5 g, 0.077 mol) in triethylamine (23.3 g, 0.23 mol) and 400 mL of methylene chloride was added trifluoroacetic anhydride (21.0 g, 0.100 mol) rapidly at 0° C. The reaction was completed after a few minutes. 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 to give 9.18 g of 3-cyano-5-methylpyridine crude, which was used in the next step without purification.

Aufarbeitung

  1. waitThe reaction was completed after a few minutes
  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

Quellen und Nachweise

ORD-Eintrag
ord-d1c3b91e71484f2d82642aba7926461a
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613789B2

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