3-Chloro-2-methylaniline → HCID 23674139, compound

Participants

Reaction Steps

Chlorosulfonic acid (516 μl, 7.77 mmol) in chloroform (5 ml) was added dropwise to a solution of 3-chloro-2-methylaniline (844 μl, 6.98 mmol) and TEA (7.8 ml, 56.54 mmol) in chloroform (20 ml) at 0° C. The mixture was stirred for 90 min, concentrated in vacuo and a solution of NaOH (848 mg, 21.2 mmol) in water (10 ml) was added and the mixture stirred for 30 min at room temperature. The reaction was concentrated in vacuo and azeotroped with toluene. The solid obtained was heated in EtOH (50 ml) at 60° C. for 15 min, concentrated in vacuo and EtOAc (50 ml) added. The resulting solid was collected by filtration and the filtrate allowed to stand at room temperature for 4 h. The crystals formed were filtered, washed with EtOAc, and the solids combined to give the title compound (1.44 g, 84%).

Provenance & Evidence