Methyl iodide → 2-Chloro-5-methoxypyridine

Participants

Reaction Steps

28% Sodium methoxide-methanol (2.0 mL) was added dropwise to the above-obtained 2-chloro-5-hydroxypyridine (1.30 g) and methyl iodide (1.25 mL) in N,N-dimethylformamide (26 mL), followed by stirring at room temperature for 1.5 hours. The reaction mixture was partitioned by use of saturated aqueous ammonium chloride and ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was purified through silica gel chromatography (hexane-ethyl acetate), to thereby give 2-chloro-5-methoxypyridine as a solid (1.40 g, 98%).

Provenance & Evidence