Thiophenol → HCID 59598389, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL sealed tube under N2, were dissolved 4-chloro-7-methoxyquinoline (1.00 g, 5.16 mmol), thiophenol (0.528 ml, 5.16 mmol) and cesium carbonate (2.52 g, 7.75 mmol) in 5 mL of DMSO then heated at 100° C. After 2 h, the crude reaction mixture was directly purified by MPLC (ISCO, dichloromethane:MeOH 100:0 to 90:10) to afford 7-methoxy-4-(phenylthio)quinoline (1.32 g, 95.6% yield) as an off-white solid. MS (ESI pos. ion) m/z: 268 (MH+). Calc'd exact mass for C16H13NOS: 267. 1H NMR (400 MHz, CDCl3): 8.49 (d, J=4.93 Hz, 1 H), 8.13 (d, J=9.22 Hz, 1 H), 7.56-7.62 (m, 2 H), 7.45-7.53 (m, 4 H), 7.23-7.29 (m, 1 H), 6.68 (d, J=4.93 Hz, 1 H), 3.98 (s, 3 H).

Provenance & Evidence