Ammonium formate → 4-(4-Amino-2-fluorophenoxy)quinolin-7-ol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-(benzyloxy)-4-(2-fluoro-4-nitrophenoxy)quinoline (16.38 g, 42 mmol) and HCOONH4 (26.46 g, 420 mmol) in a mixture solution of EtOH/H2O (84 mL, v/v=4:1) was added a catalytic amount of Pd/C (0.50 g, 5% amount, 53%˜55% water content, w/w). The reaction was stirred at 30° C. for 24 hours, and was monitored by LC-MS. After the complete consumption of 7-(benzyloxy)-4-(2-fluoro-4-nitrophenoxy)quinoline, 6 M HCl (80 mL) was added to the reaction mixture until the solid was dissolved. The resulted solution was filtered. Saturated aqueous NaHCO3 solution (210 mL) was added to the filtrate to adjust the final pH to 6.0˜6.5 followed by the addition of a mixture of water (20 mL) and CH2Cl2 (50 mL). The resulted mixture was stirred at room temperature for 4 hours. The solid was collected by filtration, washed with a mixture of MeOH/DCM (50 mL, v/v=1/1), and dried in vacuo at 45° C. to give the title compound as a light yellow solid (11.0 g, 92%).

Provenance & Evidence