General procedure for the synthesis of 7-methoxyquinoline from 7-hydroxyquinoline and iodomethane: 7-hydroxyquinoline (8 g, 55.11 mmol) was added to a solution of sodium hydride (5.5 g, 137.50 mmol, 60% pure) in N,N-dimethylformamide (150 mL). The reaction mixture was stirred in a water/ice bath at 0 °C for 1 hour. Subsequently, iodomethane (7.84 g, 55.23 mmol) was added and the reaction solution was continued to be stirred at room temperature for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of a water/ice mixture (700 mL) and extracted with ethyl acetate (3 x 200 mL). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography, using a petroleum ether solution of 6% ethyl acetate as eluent to give 7-methoxyquinoline as a red oil (5.5 g). The product was analyzed by LC-MS showing [M+H]+ peak of 160.0. 1H-NMR (300 MHz, CDCl3) data were as follows: δ 8.84-8.86 (m, 1H), 8.07-8.11 (m, 1H), 7.70-7.73 (t, J = 5.1 Hz, 1H), 7.44 (d, J = 2.4 Hz, 1H). 7.20-7.30 (m, 2H), 3.95 (s, 3H). Case No. BIOE0009-401-PC.
