Hydrogen Bromide → 7-Hydroxy-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

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Reaction Steps

Hydrobromic acid (80 mL, 1467 mmol) was added slowly to a solution of methyl 3-methyl-6-[(1-methylethyl)sulfonyl]-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (14.13 g, 29.3 mmol) in acetic acid (30 mL). The mixture was heated to reflux for 5 days. The mixture was cooled to room temperature and diluted with water. The solids were collected by filtration, washed with water, and dried to afford 7-hydroxy-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (12.5 g, 94% yield). 1H NMR (400 MHz, DMSO-d6) δ11.73 (br. s., 1H), 8.31 (s, 1H), 7.94-8.00 (m, 2H), 7.91 (d, J=7.78 Hz, 1H), 7.79 (t, J=7.65 Hz, 1H), 7.54 (s, 1H), 3.91 (dt, J=6.81, 13.74 Hz, 1H), 2.35 (s, 3H), 1.22 (s, 3H), 1.21 (s, 3H); MS (m/z) 454.1 (M+H+).

Provenance & Evidence