Reaktion #518636

Reaktionsgleichung

4-chloro-3-nitroquinoline

triethylamine

tert-butyl 2-(2-aminoethoxy)ethylcarbamate

→

tert-butyl 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethylcarbamate

Ausbeute 76.7%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe reaction mixture was washed with H2O (2×300 mL) and brine (300 mL)
2. 2
   TrocknenThe organic portion was dried over Na2SO4
3. 3
   Einengenconcentrated
4. 4
   Sonstigeto give a bright yellow solid
5. 5
   SonstigeRecrystallization from ethyl acetate/hexanes

Vorschrift

A stirred solution of 4-chloro-3-nitroquinoline (31.4 g, 0.151 mol) in 500 mL of anhydrous CH2Cl2, under N2, was treated with triethylamine (43 mL, 0.308 mol) and tert-butyl 2-(2-aminoethoxy)ethylcarbamate (0.151 mol). After stirring overnight, the reaction mixture was washed with H2O (2×300 mL) and brine (300 mL). The organic portion was dried over Na2SO4 and concentrated to give a bright yellow solid. Recrystallization from ethyl acetate/hexanes gave 43.6 g of tert-butyl 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethylcarbamate as bright yellow crystals.

Quelle