Dimethyl acetylenedicarboxylate → Dimethyl 5-chloro-1-(4-methoxybenzyl)-6-oxo-1,6-dihydropyridine-3,4-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

Compound (8) (2.0 g, 7.01 mmol) and 2-butynedioic acid dimethyl ester (2.99 g, 21.04 mmol) were added to xylene (40 ml). The reaction was heated at about 150° C. for about 16 h. The reaction was cooled to about 25° C. The reaction mixture was filtered through a Büchner funnel to afford the title compound (0.9 g, 2.338 mmol, 33.3% yield). LC-MS (ESI+): m/e 366 (M+H)+, Rt: 1.98 min; 1H-NMR (DMSO-d6, 400 MHz): δ=3.73 (s, 3H), 3.79 (s, 3H), 3.88 (s, 3H), 5.21 (s, 2H), 6.91 (d, 2H, J=6.8 Hz), 7.34 (d, 2H, J=6.8 Hz), 8.81 (s, 1H).

Provenance & Evidence