Pyridinium chloride → [4-(4-Hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone

Participants

Reaction Conditions

Reaction Steps

A mixture of [4-(4-methoxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (1.3 g, 3.3 mmol) and pyridine HCl(10 g) was heated to 200° C. After 1 hr, the reaction was cooled and then diluted with 2N HCl. The acidic layer was extracted with EtOAc, dried and concentrated to give an oil which was triturated with 10% EtOAc/hexane to give a solid which was collected by filtration to give ([4-(4-hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (0.80 g, Yield=68%); MS (ESI) m/z 394 ([M+H]+); 1H NMR (DMSO) δ 9.72 (bs, 1H), 9.08 (s, 1H), 8.31 (d, 1H, J=6.8 Hz), 8.06 (d, 1H, J=8.6 Hz), 7.80-7.75 (m, 1H), 7.62-7.60 (m, 2H), 7.58-7.54 (m, 1H), 7.38-7.35 (m, 2H), 7.13 (d, 2H, J=7.8 Hz), 6.75 (d, 2H, J=7.8 Hz);

Provenance & Evidence