Ammonium Chloride → 4-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamine

Participants

Reaction Steps

To a solution of 4-(2-fluoro-4-nitrophenoxy)-6,7-dimethoxyquinoline (16.0 g, 0.046 mol) and NH4Cl (6.0 g, 0.11 mol) in EtOH/H2O (150 mL, v/v=4:1) was added iron powder (12.4 g, 0.22 mol) at rt. The reaction mixture was heated to reflux for 2 h, then cooled down to rt. Celite (10 g) was then added and stirring for 30 min. The mixture was filtered and the solid was washed with MeOH (20 mL×3) and DCM (20 mL×3). The filtrate was washed with 30 mL of saturated NaHCO3 aqueous. The aqueous phase was extracted with DCM (20 mL×3). The combined organic phases were washed with brine (20 mL×3), dried over Na2SO4, and concentrated in vacuo to give a yellow solid (0.9 g, 98%).

Provenance & Evidence