Methyl iodide → 7-Methoxyquinoline

Participants

Reaction Conditions

Reaction Steps

A suspension of NaH (3.3 g; 137.93 mmol) in anhydrous DMF (160 ml) was cooled to 0° C. with stirring under argon. 7-Quinolinol (8 g; 55.17 mmol) dissolved in anhydrous DMF (320 ml) was added and the mixture was stirred at 0° C. under argon for 1 h. The mixture was then allowed to warm to rt and MeI (7.8 ml; 55.17 mmol) was added and the reaction was stirred for 1 h. Ice water was then added cautiously and the resulting mixture extracted with EtOAc (3×500 ml). The organic layer from this extraction was then washed with water (400 ml) and brine (400 ml). The resulting organic layer was dried with MgSO4 and solvents removed to afford the desired compound (8.76 g; 99%)

Provenance & Evidence