Water → 5-Bromo-1-(2-methoxyethyl)-3-nitropyridin-2(1H)-one

HRID 271962

Reaktionsgleichung

Reaktionsgleichung von HRID 271962
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[C:11]([OH:14])=[N:12][CH:13]=1.[CH3:18][O:19][CH2:20][CH2:21]Br.O>CN(C)C=O>[Br:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[C:11](=[O:14])[N:12]([CH2:21][CH2:20][O:19][CH3:18])[CH:13]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl ether2×HCID 178418997HCID 178418997, Verbindung

Produkt 1

HCID 222932795-Bromo-1-(2-methoxyethyl)-3-nitropyridin-2(1H)-oneAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Cesium carbonate (14.88 g, 45.66 mmol) was added to a solution of 5-bromo-3-nitropyridin-2-ol (10.0 g, 45.7 mmol) and 2-bromoethyl methyl ether (4.29 mL, 45.66 mmol) in N,N-dimethylformamide (400 mL). After 3 h, additional 2-bromoethyl methyl ether (4.29 mL, 45.7 mmol) was added, and the reaction was heated to 60° C. After 4 h, water was added. The mixture was extracted with ethyl acetate (3×), and the combined organic extracts were washed with saturated brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→40% ethyl acetate/hexanes) gave the title compound (7.39 g). MS 277 (M).

Aufarbeitung

  1. waitAfter 4 h
  2. extractionThe mixture was extracted with ethyl acetate (3×)
  3. washthe combined organic extracts were washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% hexanes→40% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8e3b46be6f5448cc8d61cbf7b6f6ac79
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452903B2

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