2-Chloro-N-methoxy-N-methylisonicotinamide → 1-(2-Chloropyridin-4-yl)ethan-1-one

HRID 859101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 859101
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=1)[C:5](N(OC)C)=[O:6].[CH3:14][Mg]Br>C1COCC1>[C:5]([C:4]1[CH:11]=[CH:12][N:13]=[C:2]([Cl:1])[CH:3]=1)(=[O:6])[CH3:14]

Komponenten

4

Edukt 2

HCID 185068942-Chloro-N-methoxy-N-methylisonicotinamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 131452551-(2-Chloropyridin-4-yl)ethan-1-oneAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-N-methoxy-N-methyl-isonicotinamide (20 g, 100 mmol) in THF (100 mL) is added a solution of methyl magnesium bromide (3M in THF, 73 mL, 220 mmol) at −40° C. After stirring the mixture for 2 hours at this temperature, the mixture is quenched with ice-cooled saturated ammonium chloride solution (300 mL). The organic phase is separated. The aqueous layer is extracted with ethyl acetate (2×150 mL). The combined organic layers are washed with brine and dried over sodium sulfate, filtered and concentrated under reduced pressure to give 4-acetyl-2-chloro-pyridine (14.4 g), which is used for the next reaction without further purification; ESI-MS (m/z): 156.0 (M++H).

Aufarbeitung

  1. customthe mixture is quenched with ice-
  2. temperaturecooled saturated ammonium chloride solution (300 mL)
  3. customThe organic phase is separated
  4. extractionThe aqueous layer is extracted with ethyl acetate (2×150 mL)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e8f9c522035a43ee8d80a77ea7edc94a
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151096B2

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