Methyl iodide → Methyl 5-chloro-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

Participants

Reaction Steps

To a suspension of 5-chloro-2-hydroxynicotinic acid (2.0 g, 12 mmol) and cesium carbonate (8.2 g, 26 mmol) in 50 mL DMF was added MeI (1.6 ml, 26 mmol). The reaction was allowed to stir for approximately 12 h. The cloudy yellow mixture was added to EtOAc/water. The organic layer was removed and the aqueous layer was extracted three times with EtOAc. The combined organic layers were washed once with water and brine, dried with Na2SO4, filtered, and concentrated to give an orange-yellow solid. The material was partitioned between 1N HCl and EtOAc. The organic layer was washed twice with 1N HCl, dried with Na2SO4, filtered, and concentrated to give the desired product as an orange solid. MS (m/z): 202.0 (M+H)+. Calc'd for C8H8ClNO3: 201.61.

Provenance & Evidence