Acetic Acid → {4-[({3-[3-Benzoyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenyl}Amino)Methyl]Phenyl}Acetic Acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate (0.06 g, 0.11 mmol) in THF/methanol/water (2:1:1, 10 mL) was added lithium hydroxide monohydrate (0.06 g, 1.4 mmol). The reaction was stirred at 40° C. for 1 h. The reaction mixture was made acidic (pH 6) with glacial acetic acid, and the solid was collected and dried over P2O5 to give the title compound as an orange solid (0.05 g, 93%): MS (EI) m/z 541.3 (M+H)+; 1H NMR (DMSO-d6): δ 3.53 (s, 2H), 4.12 (d, J=5.8 Hz, 2H), 6.35-6.55 (m, 4H), 6.97 (t, J=7.4 Hz, 1H), 7.15-7.22 (m, 4H), 7.36 (t, J=7.8 Hz, 2H), 7.55 (t, J=7.4 Hz, 1H), 7.61 (d, J=8.2 Hz, 2H), 7.72 (t, J=8.0 Hz, 1H), 7.98 (d, J=8.0 Hz, 1H), 8.29 (d, J=7.1 Hz, 1H), 9.08 (s, 1H).

Provenance & Evidence