Acetic Anhydride → Ethyl 3-acetamido-6-bromopyridine-2-carboxylate

HRID 1478542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478542
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1.[CH3:14][C:15](OC(C)=O)=[O:16]>C1COCC1>[C:15]([NH:1][C:2]1[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1)(=[O:16])[CH3:14]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 25137688Ethyl 3-amino-6-bromopicolinate

Produkt 1

HCID 90044467Ethyl 3-acetamido-6-bromopyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of ethy 3-amino-6-bromo-pyridine-2-carboxylate (10 g, 40.8 mmol) in THF (50 ml) was added Ac2O (12 ml, 127.8 mmol) at ambient temperature then the solution was heated to 60° C. for 3 h. The solution was allowed to cool to ambient temperature then concentrated under reduced pressure and dissolved in ethyl acetate. This afforded the product in crystalline form. The mother liquor was purified using flash chromatography eluting with ethyl acetate/heptane, gradient, giving ethyl 3-acetamido-6-bromo-pyridine-2-carboxylate as a yellow solid.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. concentrationthen concentrated under reduced pressure
  3. dissolutiondissolved in ethyl acetate
  4. customThis afforded the product in crystalline form
  5. customThe mother liquor was purified
  6. washeluting with ethyl acetate/heptane, gradient

Quellen und Nachweise

ORD-Eintrag
ord-46b8dc6fbfac48ff9e24f31653117241
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403845B2

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