Water → 2-{[2-Methyl-3-(methyloxy)phenyl]oxy}-5-nitropyridine

HRID 1505348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505348
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:10].[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1.O>CN(C=O)C>[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:10][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 2489133-Methoxy-2-methylphenol2×

Produkt 1

HCID 672360642-{[2-Methyl-3-(methyloxy)phenyl]oxy}-5-nitropyridineAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-methyl-3-(methyloxy)phenol (Intermediate 59, 1.3 g) in DMF (50 mL) was added sodium hydride (60% in mineral oil, 480 mg, 0.012 molat 0° C. and the mixture was stirred for 30 minutes. 2-Chloro-5-nitropyridine (1.9 g, 0.012 mol, Aldrich) was added and the mixture was heated at 60° C. for 3 hours. The mixture was poured into H2O (100 mL) and extracted with ethyl acetate (4 times 100 mL). The combined ethyl acetate phases were dried over sodium sulphate and concentrated under vacuum to give a residue which was purified by column chromatography on silica gel (PE:EtOAc=10:1) to afford the title compound (2.3 g) as a liquid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (4 times 100 mL)
  2. dry with materialThe combined ethyl acetate phases were dried over sodium sulphate
  3. concentrationconcentrated under vacuum
  4. customto give a residue which
  5. customwas purified by column chromatography on silica gel (PE:EtOAc=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-481eba1112314e74b75583c57956413b
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216967B2

Notizen zur Reaktion

Wird geladen…