Pyridinium chloride → HCID 44254688, compound

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Reaction Steps

To a melted pyridine hydrochloride (15.0 g) at 160-180° C. was added 2-(3-methoxyphenyl)benzofuran-5-carbonitrile (120) in one portion and the stirring continued at 180° C. for 2.5 h. The mixture was cooled down, diluted with water (100 mL) and 1 M HCl (50 mL) and stirred at room temperature for 30 min. A precipitate formed was separated, washed with 1 M HCl (150 mL) and water (150 mL) and dried. The residue was purified by flash chromatography (silica gel, EtOAc/hexanes 1/3) followed by recrystallization to give 125 as white solid (1.50 g, 69%): mp 222-224° C. (EtOAc/hexanes). 1H NMR (DMSO-d6) δ9.78 (d, J=1.1 Hz, 1H), 8.21 (br s, 1H), 7.85 (d, J=8.2 Hz, 1H), 7.75 (ddd, J=8.2, 1.6, 1.1 Hz, 1H), 7.48 (s, 1H), 7.40 (dd, J=8.2, 1.1 Hz, 1H), 7.33 (dd, J=8.2, 7.7 Hz, 1H), 6.86 (ddd, J=8.2, 2.2, 1.1 Hz, 1H). HPLC (method B) tR 5.70 min (100.0 area %). Anal. (C15H9NO2) C, H, N.

Provenance & Evidence