Reaktion #1439769

Reaktionsgleichung

water

sodium hydride

phenol

[2-(benzyloxy)ethyl]-(2-chloro-6-methyl-3-nitropyridin-4-yl)amine

→

[2-(benzyloxy)ethyl]-(6-methyl-3-nitro-2-phenoxy-pyridin-4-yl)amine

Ausbeute 90.0%

Lösungsmittel

ethyl acetate

diglyme

diglyme

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe addition flask was rinsed with additional diglyme (2×5 mL), which
2. 2
   workup.ADDITIONwas added to the reaction flask
3. 3
   Temperaturthe resulting dark solution was heated at 60° C. for 90 minutes
4. 4
   Temperaturto cool
5. 5
   workup.STIRRINGstirred rapidly for 90 minutes
6. 6
   SonstigeA yellow solid formed
7. 7
   Sonstigewhich was isolated by filtration
8. 8
   TrocknenThe solution was then dried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    Sonstigeto provide a yellow oil, which
12. 12
    Sonstigeto crystallize over three days
13. 13
    SonstigeThe product was triturated with hexane
14. 14
    Sonstigethe resulting solid was isolated by filtration
15. 15
    Sonstigedried for two hours under high vacuum at 55° C.

Vorschrift

Under a nitrogen atmosphere, diglyme (20 mL) was added to sodium hydride (0.548 g, 13.7 mmol), which is available as a 60% dispersion in mineral oil, and the mixture was cooled to 0° C. A solution of phenol (1.35 g, 14.4 mmol) in diglyme (20 mL) was added, and the addition flask was rinsed with additional diglyme (2×5 mL), which was added to the reaction flask. The reaction became homogeneous and was stirred for 30 minutes. Solid [2-(benzyloxy)ethyl]-(2-chloro-6-methyl-3-nitropyridin-4-yl)amine (4.2 g, 13 mmol) was added, and the resulting dark solution was heated at 60° C. for 90 minutes. The reaction was allowed to cool and then slowly poured into water (500 mL) and stirred rapidly for 90 minutes. A yellow solid formed, which was isolated by filtration and dissolved in ethyl acetate. The solution was then dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a yellow oil, which began to crystallize over three days. The product was triturated with hexane, and the resulting solid was isolated by filtration and dried for two hours under high vacuum at 55° C. to provide 4.44 g of [2-(benzyloxy)ethyl]-(6-methyl-3-nitro-2-phenoxy-pyridin-4-yl)amine as a yellow solid.

Quelle