Pyridine → 3-Amino-4-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)quinolin-2(1H)-one

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Reaction Steps

A mechanically stirred solution of N-[2-[(5-chloro-2-methoxyphenyl)carbonyl]-4-(trifluoromethyl)phenyl]chloroacetamide (12.2 g, 0.03 mol) in anhydrous pyridine (150 mL) was heated to reflux for 20-25 min. The resultant suspension of the pyridinium salt was allowed to cool and then diluted with benzene (100 mL). The pyridinium salt was filtered, washed with benzene and then dried in vacuo to afford the desired titled compound (13.75 g, 98%): mp 325-330° C. (dec.); IR (KBr, cm-1) 1678,1322,1270,1118; 1H NMR (300 MHz, DMSO-d6)δ 3.59 (3H, s), 7.09 (1H, d, J=9.0 Hz), 7.38 (1H, s), 7.44 (1H, d, J=2.6 Hz), 7.52 (1H, dd, J=8.9 and 2.6 Hz), 7.83 (1H, d, J=8.7 Hz), 8.11 (1H, dd, J=8.7 and 1.8 Hz), 8.19-8.27 (2H, m), 8.70-8.75 (1H, m), 9.05-9.07 (2H, m), 13.54 (1H, brd s); MS m/e 431 (MH)+.

Provenance & Evidence