Thionyl Chloride → HCID 57556155, compound

Participants

Reaction Steps

Prepared according to Procedure B using 8-methyl-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde (1.6541 g, 5.25 mmol) and solid NaBH (0.2977 g, 7.87 mmol, 1.5 eq) in THF (26 mL) followed by Procedure C using the crude (8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol and SOCl2 (1.9 mL, 26.23 mmol, 5 eq) in CHCl3 (26 mL). After purification, 3-(chloromethyl)-8-methyl-2-(2-(trifluoromethyl)phenyl)quinoline was obtained as yellow syrup. 1H NMR (DMSO-d6) δ ppm 8.60 (1 H, s), 7.92 (2 H, dd, J=11.5, 8.0 Hz), 7.72-7.85 (2 H, m), 7.67 (2 H, dd, J=14.3, 7.2 Hz), 7.54-7.62 (1 H, m), 4.71 (2 H, dd, J=89.8, 11.9 Hz), 2.62 (3 H, s). Mass Spectrum (ESI) m/e=336.1 (M+1).

Provenance & Evidence