Chlorosuccinimide → HCID 86656171, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 8-hydroxy-N-methoxy-N-methylquinoline-7-carboxamide (5.00 g, 21.5 mmol) in acetic acid (100 mL) was added N-chlorosuccinimide (3.16 g, 23.7 mmol) and the resulting mixture heated at 100° C. for 18 hours. After allowing the mixture to cool to ambient temperature, the reaction mixture was concentrated in vacuo, then neutralized with saturated sodium bicarbonate, and then extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and then concentrated to dryness under reduced pressure. The residue was purified on silica gel, eluting with 0 to 10% methanol in dichloromethane, to give the desired product (4.68 g, 81%). LCMS calculated for C12H12ClN2O3(M+H)+: m/z=267.1; found: 267.0. 1H NMR (DMSO-d6, 400 MHz) δ 90.4 (1H, dd, J=4.0 and 1.2 Hz), 8.61 (1H, dd, J=8.8 and 1.6 Hz), 7.92 (1H, s), 7.80 (1H, dd, J=8.8 and 4.4 Hz), 3.45 (3H, s), 3.30 (4H, br s) ppm.

Provenance & Evidence