Water → 5-Methylnicotinonitrile

HRID 1352988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352988
[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 10 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-8a512d0327eb46f48604ce723605f59c
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220770B2

Notizen zur Reaktion

Wird geladen…