Ethanol → Ethyl 6-chloronicotinate

Participants

Reaction Steps

To 6.85 g (44 mmol) of 6-chloronicotinic acid dissolved in 50 mL of tetrahydrofuran was added ethanol (6 mL), dimethylaminopyridine (700 mg) and 1-(3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (EDCl) (9.4 g, 49 mmol). The reaction was stirred at ambient temperature for 4 hours and then concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with water (2×), saturated sodium bicarbonate (2×) and brine, dried over sodium sulfate and concentrated in vacuo. The residue obtained was flash chromatographed on silica gel eluting with 10% ethyl acetate in hexane to afford 6.00 g of the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 1.40 (t, 3H), 4.40 (q, 2H), 7.40 (d, 1H), 8.25 (dd, 1H), 9.00 (d, 1H). MS (DCl/NH3) m/e 186/188 (M+H)+, 203/205 (M+H+NH3 )+.

Provenance & Evidence