Ammonia → Methyl 2-amino-6-chloronicotinate

HRID 505067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505067
Cl[C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH3:13]>CC(C)=O.CO>[NH2:13][C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 11106516Methyl 2,6-dichloropyridine-3-carboxylate

Produkt 1

HCID 57415887Methyl 2-amino-6-chloronicotinateAusbeute 148,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21894497Aceton-methanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Performed in duplicate on identical scales in two pressure vessels, methyl 2,6-dichloronicotinate (4.5 g, 22 mmol) was dissolved in NH3 solution (250 mL, 0.5 M in 1,4-dioxane; 0.125 mol). The pressure vessels were sealed and heated at (85±5) ° C. for 9 days. The two reaction mixtures were allowed to cool to 25° C., then combined and concentrated under reduced pressure to yield a white solid. Dissolution of the solid in 1:1 acetone-MeOH (˜500 mL), followed by adsorption onto silica gel (25 g) and then purification by flash column chromatography (25:10:1 hexane-CH2Cl2-Et2O), gave 6.08 g (75%) of methyl 2-amino-6-chloronicotinate.

Aufarbeitung

  1. customThe pressure vessels were sealed
  2. customThe two reaction mixtures
  3. concentrationconcentrated under reduced pressure
  4. customto yield a white solid
  5. custompurification by flash column chromatography (25:10:1 hexane-CH2Cl2-Et2O)

Quellen und Nachweise

ORD-Eintrag
ord-e85610a327114483a7fc57648e12affd
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781437B2

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