2-(4-Chloro-benzyl)-3-hydroxy-8-phenyl-quinoline-4-carboxylic Acid → 8-(sec-butyl)-2-(4-chlorobenzyl)-3-hydroxyquinoline-4-carboxylic Acid

Participants

Reaction Steps

This compound was synthesized by the procedure described above for Compound 2, reacting 7-sec-butylisatin (1.00 g, 4.92 mmol) with 3-(4-chlorophenyl)-2-oxopropyl acetate (1.39 g, 6.15 mmol). The crude acid was purified as described above for Compound 3 and, after hydrochloric acid treatment of an acetonitrile/water solution of the triethylammonium salt, extracted into ethyl acetate (3×), washed with brine, dried over anhydrous magnesium sulfate, filtered, evaporated and lyophilized. It was then purified (preparative HPLC, eluting with acetonitrile/water/triethylamine), and converted back to the free acid and extracted and evaporated once more as described above. A final lyophilization step gave product Compound 10 as a fluffy, bright yellow solid (72 mg, 3.9% yield): 1H NMR (400 MHz, DMSO-D6) δ 0.74 (t, J=7.3 Hz, 3H) 1.22 (d, J=6.8 Hz, 3H) 1.61 (m, 2H) 3.91 (m, 1H) 4.32 (dd, 2H) 7.34 (m, 4H) 7.39 (d, J=6.1 Hz, 1H) 7.51 (dd, J=8.6, 7.3 Hz, 1H) 8.25 (dd, J=8.3, 1.3 Hz, 1H); HRMS (ESI/FTMS) calcd for C21H21ClNO3 (MH+) 370.1205, found 370.1204. Anal. Calcd for C21H20ClNO3: C, 68.20; H, 5.45; N, 3.79. Found: C, 67.97; H, 5.47; N, 3.53.

Provenance & Evidence