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0 °C

To a round-bottomed flask containing 7-bromo-4-chloro-3-nitroquinoline (60 g, 209.1 mmol) was added DMF (390 mL) and triethylamine (44 mL, 313.6 mmol) and the solution was stirred at 0° C. in an ice-bath. To this cooled solution was added 3-aminopropan-1-ol (17.6 mL, 230.0 mmol) and the reaction was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the resultant orange solid was recrystallized from ethyl acetate (800 mL). The product was separated by filtration and the solids were washed with diethyl ether and dried under reduced pressure to afford crude 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propan-1-ol (88.15 g) as a brown solid.

1. stirringthe reaction was stirred at ambient temperature overnight
2. customThe solvent was removed under reduced pressure
3. customthe resultant orange solid was recrystallized from ethyl acetate (800 mL)
4. customThe product was separated by filtration
5. washthe solids were washed with diethyl ether
6. customdried under reduced pressure