Water → HCID 68899031, compound

Participants

Reaction Steps

A mixture of 2-mercaptobenzyl alcohol (1.78 g, 12.7 mmol), 2,6-dichloroquinoline (2.48 g, 12.5 mmol) and potassium carbonate (1.73 g, 12.5 mmol) in N,N-dimethylformamide (25 mL) was stirred at room temperature under nitrogen for 3 hours, then at 60° C. for 17 hours. The cooled reaction mixture was poured into water and extracted with ethyl acetate (x2). The combined organic layers were washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash column chromatography on silica, eluting with 5-10% ethyl acetate/dichloromethane, to give {2-[(6-chloroquinolin-2-yl)thio]phenyl}methanol (0.37 g, 9%) as a colourless oil. 1H NMR (400 MHz, CDCl3) δ 7.84 (1H, d, J=8.7 Hz), 7.72-7.66 (4H, m), 7.55-7.51 (2H, m), 7.39-7.35 (1H, m), 7.19 (1H, dd, J=1.2, 8.7 Hz), 4.84 (2H, s), 3.78 (1H, s); m/z (ES+) 302, 304 [MH+].

Provenance & Evidence