Aniline → trans-9-Bromo-6-methyl-5-phenylcarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Participants

Reaction Steps

A procedure similar to that described in Example 5 was carried out with trans-9-bromo-5-carboxymethyl-6-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (100 mg, 0.283 mmol) and aniline (28 mL, 0.311 mmol) to give 112 mg of the title compound (92%): mp>300° C.; 1H NMR (270 MHz, DMSO-d6) δ12.08 (s, 1H), 9.99 (s, 1H), 7.55 (d, 2H, J=7.6 Hz), 7.30 (t, 2H, J=7.6 Hz), 7.21 (s, 1H), 7.17 (s, 1H), 7.05 (t, 1H, J=7.6 Hz), 4.92~5.02 (m, 1H), 3.25 (dd, 1H, J=17.8, 5.9 Hz), 2.50~2.66 (m, 3H), 2.28~2.42 (m, 1H), 0.86 (d, 3H, J=6.9 Hz).

Provenance & Evidence