Thionyl Chloride → 5-(chloromethyl)-N-(3,4-dichlorobenzyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (0.103 mL, 1.413 mmol) was added to a suspension of (6-((3,4-dichlorobenzyl)amino)pyridin-3-yl)methanol (0.1 g, 0.353 mmol) in DCM (3.5 mL) cooled to 0° C. The mixture was stirred for 18 h at room temperature. The resulting white suspension was concentrated to yield 5-(chloromethyl)-N-(3,4-dichlorobenzyl)pyridin-2-amine, used in the next step without purification. 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.05 (1H, dd, J=9.29, 2.01 Hz), 7.92-8.01 (1H, m), 7.54-7.65 (2H, m), 7.36 (1H, dt, J=8.28, 1.00 Hz), 7.04-7.23 (1H, m), 4.65 (1H, s), 4.61 (2H, d, J=2.76 Hz), 4.39 (1H, s). LCMS: R.T.=2.96; [M+H]+=301.02.

Provenance & Evidence