Water → Methyl 2-methoxyisonicotinate

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, to a solution of 2-chloroisonicotinic acid (10.0 g) in DMF (150 mL) was added a 28% solution of sodium methoxide in methanol (38.6 mL), and the mixture was stirred at 130° C. for 14 hr. Iodomethane (15.9 mL) was added to the reaction mixture at 80° C., and the mixture was stirred at 80° C. for 5 min. Water was added at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, and dried over anhydrous magnesium sulfate. After silica gel filtration, the solvent was evaporated under reduced pressure to give a crude product of the title compound (8.57 g) as a pale-yellow oil. This compound was used for the next step without further purification.

Provenance & Evidence