Acetic Acid → HCID 117736931, compound

Participants

Reaction Conditions

Reaction Steps

A 250-mL RBF was charged with (E)-ethyl 3-(5-(benzylthio)-2-((2-bromo-4-chlorophenyl)amino)phenyl)acrylate (10.4 g, 20.68 mmol) and MeOH (103 ml) to give a thick, yellow suspension. Sodium methoxide (25 wt % in MeOH) (0.894 ml, 4.14 mmol) was added. A reflux condenser was attached, and the flask was heated to 80° C. overnight. The mixture was cooled to room temperature. Acetic acid (1.776 ml, 31.0 mmol) was added, and the mixture was concentrated. The residue was taken up in 2-PrOH and heated to boiling to give a brown solution. The mixture was cooled to room temperature with stirring then was concentrated. The residue was taken up in DCM and loaded onto a 25-g silica gel loading column. The column was eluted directly onto a pre-equilibrated 120-g Redi-Sep silica gel column with 0-50% EtOAc/Heptane to give a solid. The solid was taken up in heptane and filtered. The filtered solid was washed with heptane and dried under a stream of N2 (g) to give 6-(benzylthio)-1-(2-bromo-4-chlorophenyl)quinolin-2(1 H)-one (5.816 g, 12.73 mmol, 61.6% yield) as a tan solid. 1 H NMR (400 MHz, DMSO-d6)□=8.09 (d, J=2.3 Hz, 1 H), 8.01 (d, J=9.5 Hz, 1 H), 7.83 (d, J=2.2 Hz, 1 H), 7.72 (dd, J=2.3, 8.4 Hz, 1 H), 7.56 (d, J=8.4 Hz, 1 H), 7.41 (dd, J=2.2, 8.8 Hz, 1 H), 7.37-7.17 (m, 5 H), 6.71 (d, J=9.6 Hz, 1 H), 6.41 (d, J=8.8 Hz, 1 H), 4.25 (s, 2 H), 3.32 (s, 3 H). m/z (ESI) 456.0 (M+H)+.

Provenance & Evidence