Hydrochloric Acid → HCID 23593812, compound

Participants

Reaction Steps

A solution of 3-ethoxy-2-nitro-pyridine (0.84 g) and ethyl 2-chloropropionate (2.1 g) in DMF (8 mL) was added dropwise to a slurry of sodium hydride (0.6 g, 60% suspension in oil) in DMF (8 mL) while cooling at 0–5° C. The resulting purple-colored solution was stirred at 0–5° C. for one hr., and then at room temperature for two hrs. Dimethylsulfate (0.89 g) was added to the solution and the reaction mixture was shaken overnight. The resulting amber-colored solution was poured onto a mixture of 1N aqueous hydrogen chloride (20 mL), ice water (20 mL), and EtOAc (50 mL), and the phases were separated. The organic phase was washed with 1N aqueous sodium hydroxide, water, and brine. The solvent was evaporated to give an amber-colored oil (933 mg), which was purified by flash chromatography on silica gel, eluting with 1:4 ethyl acetate/hexanes to give 389 mg (28% yield) of a pale yellow oil. AP/MS+=283.

Provenance & Evidence