Acetic Anhydride → N-(4-Chloropyridin-2-yl)acetamide

HRID 1426993

Reaktionsgleichung

Reaktionsgleichung von HRID 1426993
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:16](=[O:18])[CH3:17])[CH:7]=1

Komponenten

4

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 5818662-Amino-4-chloropyridine

Produkt 1

HCID 22832129N-(4-Chloropyridin-2-yl)acetamideAusbeute 99 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Commercially available 2-amino-4-chloropyridine (50 g, 389 mmol) was dissolved in acetic anhydride (500 mL), triethylamine (271 mL, 1.94 mol) was added at 20° C., and the mixture was stirred at 60° C. for 12 hours. The mixture was cooled to 25° C. and then the solvent was evaporated. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=4:1-1:1) and then the target fraction was concentrated under vacuum to obtain the title compound (66 g, 99%).

Aufarbeitung

  1. temperatureThe mixture was cooled to 25° C.
  2. customthe solvent was evaporated
  3. customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=4:1-1:1)
  4. concentrationthe target fraction was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c37ec05972464ce387071ecd9eec2dbb
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933099B2

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