Chlorosuccinimide → 8-Chloro-2-methylquinolin-7-ol

Participants

Reaction Steps

Referring to FIG. 19, under a nitrogen atmosphere, 7-hydroxyquinaldine (4, 0.39 g, 2.452 mmol) was added to a solution of NCS (0.3283 g, 2.459 mmol) and zirconium chloride (0.0285 g, 0.122 mmol) in dichloromethane (35 mL). After stirring for 23 h, the solution was diluted with chloroform and washed successively with saturated sodium carbonate solution, water, and brine. The solvent was evaporated to give a brown residue, which was purified by column chromatography (1:3 EtOAc/hexane) to yield 5c (0.2612 g, 1.349 mmol, 55%) as an oily yellow residue: 1H NMR (CDCl3) δ 8.00 (1H, d, J=8.0 Hz), 7.64 (1H, d, J=9.2 Hz), 7.28 (1H, d, J=8.0 Hz), 7.23, (1H, d, J=8.4 Hz), 2.80 (3H, s); 13C NMR (CDCl3) δ 160.6, 152.8, 144.9, 136.6, 127.5, 122.7, 120.7, 117.0, 114.6, 25.9; FTIR (neat) 2926, 1619, 1509, 1437, 1343, 1267, 1215, 1141, 1002, 835, 750 cm−1; MS (ESI) m/z calculated for (C10H8ClNO+H)+ 194 (35Cl) and 196 (37Cl), found 194 (35Cl) and 196 (37Cl); HRMS (ESI) m/z calculated for (C10H8ClNO+H)+ 194.0373 (35Cl) and 196.0343 (37Cl), found 194.0362 (35Cl) and 196.0333 (37Cl).

Provenance & Evidence