Methanol → 6-Chloro-2-methoxy-3-nitropyridine

HRID 31819

Reaktionsgleichung

Reaktionsgleichung von HRID 31819
[H-].[Na+].[CH3:3][OH:4].Cl[C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([Cl:15])[N:7]=1.O>C1(C)C(C)=CC=CC=1>[Cl:15][C:8]1[N:7]=[C:6]([O:4][CH3:3])[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydrideHCID 852392,6-Dichloro-3-nitropyridine

Produkt 1

HCID 107977036-Chloro-2-methoxy-3-nitropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel3×

Versuchsvorschrift

To a suspension of sodium hydride (684 mg, 28.49 mmol) in xylene (100 ml), methanol (0.98 ml, 25.9 mmol) in xylene (30 ml) was added under nitrogen. The mixture was stirred for 20 min. A solution of 2,6-dichloro-3-nitropyridine (5.0 g, 25.9 mmo) in xylene (100 ml) was added to the reaction mixture and stirred at room temperature overnight. Water (50 ml) was added and the organic layer was separated. The organics was washed with water (1×50 ml) and brine (2×50 ml), dried, and concentrated in vacuo. The crude product was purified by flash chromatography (10:1 methylene chloride and acetone) to provide the desired compound, 6-chloro-2-methoxy-3-nitro-pyridine, as the only isomer as light yellow solid (90%).

Aufarbeitung

  1. additionwas added under nitrogen
  2. stirringstirred at room temperature overnight
  3. customthe organic layer was separated
  4. washThe organics was washed with water (1×50 ml) and brine (2×50 ml)
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (10:1 methylene chloride and acetone)

Quellen und Nachweise

ORD-Eintrag
ord-f960d4a592e84bd0a048645b99309520
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425557B2

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