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

Participants

Reaction Steps

A mixture of 4-(2-fluoro-4-nitrophenoxy)-6,7-dimethoxyquinoline (612 mg, 1.8 mmol), Zn powder (2.0 g) and NH4Cl (1.4 g) in MeOH (25 mL) and THF (25 mL) was heated at reflux temp. overnight with stirring. To this mixture was added DMF (45 mL) and water (20 mL), stirred for 10 minutes, and the solid was filtered. The filtrate solution was concentrated in vacuo, and the residue was purified by preparative HPLC to afford the product (230 mg, 41%) as a brown solid. 1H NMR (CDCl3) δ 8.38 (d, 1H, J=5.5 Hz), 7.52 (s, 1H), 7.32 (s, 1H), 6.91 (t, 1H, J=8.8 Hz), 6.44 (dd, 1H, J=11.6, 2.2 Hz), 6.38 (dd, 1H, J=8.2, 2.2 Hz), 6.32 (d, 1H, J=5.0 Hz), 3.94 (s, 3H), 3.92 (s, 3H).

Provenance & Evidence