4-Chloroaniline → HCID 90387867, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-2-chloro-5-nitropyridine (2.374 g, 10 mmol) and 4-chloroaniline (2.55 g, 20.00 mmol) in dimethylsulfoxide (20 mL) was heated at 90° C. for 2 hours. After cooling to ambient temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with 1:20 ethyl acetate/heptanes to give the crude product. This material was then triturated with 10% ethyl acetate in heptanes to give title compound (2.25 g, 6.85 mmol, 68.5% yield).

Provenance & Evidence