Methylamine → 5-chloro-2,N-dimethylbenzamide

Participants

Reaction Steps

Thionyl chloride (42.8 ml, 586 mmol) was added to 5-chloro-2-methylbenzoic acid (25.0 g, 147 mmol). The mixture was stirred under heating to reflux for 1.5 hours. Thereafter, excessive thionyl chloride was distilled away under reduced pressure. The residue was dissolved in methylene chloride (140 ml), and a 40% methylamine aqueous solution (34.2 ml, 440 mmol) was then added dropwise thereto under cooling on ice. Thereafter, the obtained mixture was stirred at 0° C. for 1 day. Thereafter, the reaction solution was extracted with ethyl acetate, and the extract was then washed with a saturated saline solution. The resultant was then dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3 to 3:2), so as to obtain 5-chloro-2,N-dimethylbenzamide (24.2 g; yield: 90%) in the form of a colorless solid.

Provenance & Evidence