Benzoic Acid → 8-Bromo-5-benzoylaminomethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

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Reaction Steps

A mixture of 8-bromo-5-aminomethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione hydrochloride (134 mg, 0.405 mmol), triethyl amine (124 μL, 0.892 mmol), benzoic acid (54 mg, 0.446 mmol), 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide (69 mg, 0.446 mmol) and N-hydroxybenzotriazole (68 mg, 0.446 mmol) in DMF (6 mL) was stirred for 20 h at room temperature and 0.1N hydrochloric acid (20 mL) was added. The precipitates formed were collected by filtration, washed with distilled water, and dried in vacuo to give 87 mg of the title compound (52%): mp 180.5°~182° C.; 1H NMR (270 MHz, DMSO-d6) δ11.86 (s, 1H), 8.56 (t, 1H, J=6 Hz), 7.34~7.54 (m, 5H), 7.12 (s, 1H), 7.17 (s, 2H), 4.96~5.06 (m, 1H), 3.90~4.00 (m, 1H), 3.72~3.82 (m, 1H), 3.43 (dd, 1H, J=17, 10 Hz), 3.19 (dd, 1H, J=17, 3 Hz).

Provenance & Evidence