Reaktion #11461

Reaktionsgleichung

2,4-dichloro-5,6-dimethyl-3-nitropyridine

Triethylamine

tert-butyl 2-aminoethylcarbamate

→

tert-butyl 2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethylcarbamate

Ausbeute 77.4%

Lösungsmittel

N,N-dimethylformamide

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 30 minutes the ice bath was removed
2. 2
   TemperaturThe reaction was heated at 60° C. overnight
3. 3
   Einengenit was concentrated under reduced pressure
4. 4
   Sonstigeto provide an orange oil
5. 5
   Waschenwashed with water (3×500 mL)
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   Sonstigeto provide a yellow oil
9. 9
   SonstigeThe oil was triturated with methanol (˜100 mL)
10. 10
    SonstigeThe resulting solid was isolated by filtration
11. 11
    Waschenwashed with cold methanol

Vorschrift

A solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (60 g, 271 mmol) in anhydrous N,N-dimethylformamide (600 mL) was cooled to 0° C. Triethylamine (44.8 mL, 326 mmol) was added drop wise followed by tert-butyl 2-aminoethylcarbamate (52.2 g, 326 mmol). After 30 minutes the ice bath was removed and the reaction mixture was heated to 60° C. The reaction was heated at 60° C. overnight and then it was concentrated under reduced pressure to provide an orange oil. The oil was dissolved in ethyl acetate (1 L), washed with water (3×500 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide a yellow oil. The oil was triturated with methanol (˜100 mL). The resulting solid was isolated by filtration and washed with cold methanol to provide 72.3 g of tert-butyl 2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethylcarbamate as a solid.

Quelle