Ethyl Acetoacetate → Ethyl 2-chloro-6-methoxy-2'-methyl-5'-oxo-1',4',5',6',7',8'-hexahydro-3,4'-biquinoline-3'-carboxylate

Participants

Reaction Steps

To a solution of 1,3-cyclohexanedione (0.56 g, 5.0 mmole) in hot ethanol (10 ml) was added 2-chloro-6-methoxy-3-quinolinecarboxaldehyde (1.1 g, 5.0 mmole) followed by ethyl acetoacetate (0.64 ml, 5.0 mmole) and finally ammonium acetate (0.77 g, 10.0 mmole). The mixture was refluxed for 12 h at which time a precipitate was observed. The reaction was cooled to room temperature, filtered and washed with ethanol then ethyl ether to provide the desired product (1.36 g, 64%) as a golden powder. 1H NMR (400 MHz; CDCl3) d 8.14 (s, 1H); 7.81 (d, 1H, J=8.9 Hz); 7.28 (dd, 1H, J=8.9, 2.7 Hz); 7.06 (d, 1H, J=2.7 Hz); 6.58 (bs, 1H); 5.48 (s, 1H); 4.10-3.95 (m, 2H); 3.89 (s, 3H); 2.42 (at, 2H, J=6.5 Hz); 2.35 (s, 3H); 2.28 (at, 2H, J=6.5 Hz); 2.0-1.80 (m, 2H); 1.13 (t, 3H, J=7.0 Hz). LC MS shows MH+ at 427 and 2M+Na at 875.

Provenance & Evidence