Acetonitrile → HCID 58964508, compound

Participants

Reaction Steps

To a suspension of NaH (315 mg, 1.4 eq) in 50 ml of tetrahydrofuran, a solution of 2-hydroxypyridine (801 mg, 1.5 eq) in 5 ml of tetrahydrofuran is added drop-wise. The mixture is stirred at room temperature for 30 min before addition of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester (1.5 g, 5.61 mmol) in 10 ml of tetrahydrofuran. The resulting mixture is stirred at room temperature for 16 hours. The solvent is removed in vacuo and the crude oil is solubilised in ethyl acetate. The organic phase is washed with sat NaHCO3 solution, dried over sodium sulfate and concentrated in vacuo to afford a crude yellow oil. The crude product is purified by flash-chromatography (ethyl acetate/hexane (0:100 to 100:0)) to obtain 2-nitro-5-(2-oxo-2H-pyridin-1-yl)-4-trifluoromethyl-benzoic acid methyl ester as a yellow solid (1.3 g, 68% yield) (ES-MS: m/z 328 [M+H+CH3CN]+, Rt 4.67 min.).

Provenance & Evidence