Methyl iodide → 7-Methoxyquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium hydride (5.5 g, 137.50 mmol, 60%) in N,N-dimethylformamide (150 ml) was added quinolin-7-ol (8 g, 55.11 mmol). The reaction was stirred for 1 h at 0° C. in a water/ice bath. Then CH3I (7.84 g, 55.23 mmol) was added and the solution was stirred for an additional 1 h at room temperature. The reaction was then quenched by the addition of water/ice (700 ml) and extracted with ethyl acetate (3×200 ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo to give a residue, which was purified by a silica gel column with 6% ethyl acetate in petroleum ether to afford 7-methoxyquinoline as a red oil (5.5 g, 63%).

Provenance & Evidence