Magnesium → HCID 69394141, compound

Participants

Reaction Steps

A mixture of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(3-methoxyphenyl)-1H-pyrrole-2,5-dione (0.73 g, 2.04 mmol), magnesium (0.89 g, 36.7 mmol) in anhydrous methanol was heated to reflux for 1.5 h. After cooling to room temperature, the light yellow solution was diluted with ethyl acetate (200 mL), washed with 1.0 M hydrochloric acid (2×50 mL), water (100 mL), dried over sodium sulfate and concentrated to provide a light brown solid. The residue was purified by column chromatography on silica gel eluting with 40-50% ethyl acetate in hexane to yield (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(3-methoxyphenyl)pyrrolidine-2,5-dione as a light yellow solid. Mp 87-91° C.; 1H NMR (CDCl3) 400 MHz δ: 8.73 (s. 1 H), 7.25-7.30 (m, 1 H), 7.14 (d, J=7.6 Hz, 1 H), 6.93-7.01 (m, 3 H), 6.77-6.86 (m, 3 H), 4.36 (d, J=6.4 Hz, 1 H), 4.24 (d, J=6.4 Hz, 1 H), 4.18 (t J=5.5 Hz, 2 H), 3.78 (s, 3 H), 2.97 (t, J=5.6 Hz, 2 H), 2.19-2.24 (m, 2 H).

Provenance & Evidence