Hydrochloric Acid → 9-Bromo-5-cyanomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

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Reaction Conditions

Reaction Steps

A mixture of 9-bromo-5-iodomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (Example 36) (632 mg, 1.5 mmol) and sodium cyanide (147 mg, 3 mmol) in DMF (5 mL) was heated at 40° C. for 14.5 h. The mixture was poured into water, acidified by addition of 1N aqueous hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with ethyl acetate to 1% acetic acid/ethyl acetate to give 117 mg of the title compound (24%): mp>280° C.; 1H NMR (270 MHz, DMSO-d6) δ12.10 (bs, 1H), 7.23 (s, 1H), 7.16 (s, 1H), 4.97~5.07 (m, 1H), 2.74~3.10 (m, 4H), 2.20 (dm, 1H, J=13.5 Hz), 1.87~2.03 (m, 1H).

Provenance & Evidence