Chloroform → HCID 66872382, compound

Participants

Reaction Steps

2-Amino-3-methoxypyridine (1.50 g) was dissolved in THF (20 mL), and at 0° C., triethylamine (3.37 mL) and 3-iodobenzoyl chloride (3.23 g) were added thereto and stirred at room temperature for 30 minutes. Triethylamine (3.37 mL) and 3-iodobenzoyl chloride (3.23 g) were further added and stirred at room temperature for 18 hours. Chloroform was added to the reaction liquid, then washed with aqueous saturated sodium hydrogencarbonate solution, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was suspended in ethyl acetate (about 50 mL) added thereto, then the solid was collected through filtration as a colorless solid (5.96 g). Methanol (50 mL) and aqueous 2 M sodium hydrogencarbonate solution (3.42 mL) were added to the obtained solid (2.00 g), and stirred at room temperature for 18 hours. Methanol was evaporated off under reduced pressure, then ethyl acetate was added to the residue, washed with water and saturated brine in that order, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 100%, gradient) to give the entitled compound (1.15 g, 80%) as an orange oil.

Provenance & Evidence