Sodium Bicarbonate → HCID 70682014, compound

Participants

Reaction Steps

A solution of 6.05 g (32.6 mmol) of methyl 2-chloro-6-methylisonicotinate (Aldrich) in 30 mL of AcOH and 30 mL of H2O2 (30 wt. % in H2O) was stirred at 135° C. for 45 min. and 9 mL of H2O2 (30 wt. % in water) was added. Heating was continued for 3 h, and saturated NaHCO3 solution was added to pH=8. The aqueous layer was extracted with EtOAc (4×), and the combined extracts were washed with 100 mL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (80% EtOAc/hexanes) provided 4.1 g of the 2-chloro-4-(methoxycarbonyl)-6-methylpyridine 1-oxide as an off-white solid in 63% yield.

Provenance & Evidence