Ethyl bromoacetate → 3-(Ethoxycarbonylmethoxy)picolinamide

HRID 914953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914953
[OH:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:16]([O:15][C:13]([CH2:12][O:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:14])[CH3:17]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 702773-Hydroxypicolinamide

Produkt 1

HCID 220385763-(Ethoxycarbonylmethoxy)picolinamideAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-hydroxy picolinic amide (10 g, 72 mmol), ethyl bromoacetate (12.02 g, 72 mmol) and anhydrous potassium carbonate (10.9 g, 79.2 mmol) in 250 ml of dry 2-butanone is heated at 80° C. for 20 hours. After cooling, the inorganic salts are filtered off and the filtrate is reduced to approximately 120 ml. After addition of cold t-butyl methyl ether the resulting precipitate is filtered off, rinsed with cold t-butyl methyl ether and dried to give 8.6 g of 3-(ethoxycarbonylmethoxy)picolinamide (53%).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe inorganic salts are filtered off
  3. additionAfter addition of cold t-butyl methyl ether the resulting precipitate
  4. filtrationis filtered off
  5. washrinsed with cold t-butyl methyl ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4e5b6d35ffee42188aa2672f0ac799a8
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265127B2

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