2-Amino-5-chlorobenzophenone → Ethyl 6-chloro-2-(chloromethyl)-4-phenyl-3-quinolinecarboxylate

Participants

Reaction Steps

To a yellow solution of 2-amino-5-chlorobenzophenone (6.93 g, 30.0 mmol) in ethanol (150 ml) was added ethyl 4-chloroacetoacetate (5.3 ml, 39.0 mmol) followed by ytterbium triflate (1.6 g, 3.0 mmol). The mixture was stirred at room temperature for 48 hours, at which time a voluminous white suspension was noted. The mixture was filtered, and the precipitate washed with ethanol, then diethyl ether, to provide ethyl 6-chloro-2-(chloromethyl)-4-phenylquinoline-3-carboxylate as a white powder (93%). 1H NMR (CDCl3; 400 MHz) δ 8.08 (d, 1H, J=8.9 Hz); 7.71 (dd, 1H, J=8.9, 2.3 Hz); 7.59 (d, 1H, J=1.95 Hz); 7.54 (m, 3H); 7.38-7.30 (m, 2H); 5.0 (s, 2H); 4.05 (q, 2H, J=7.0 Hz); 0.92 (t, 3H, J=7.0 Hz). LC MS (CI) shows M+H 360.

Provenance & Evidence