3-Chloroaniline → HCID 31698646, compound

Participants

Reaction Steps

A solution of 6-methylpicolinic acid (5.0 g, 36 mmol) in THF (60.0 ml) was treated with two drops of DMF and 3.5 ml (5.09 g, 40 mmol, 1.1 equiv.) of oxalyl chloride were added dropwise. The solution was stirred for 30 min at room temperature. The reaction mixture was then evaporated to dryness in vaccuo. The residue was taken up in 40 ml of dry THF, and cooled to 0° C. Triethylamine (6.1 ml, 4.43 g, 44 mmol, 1.2 equiv.), and a solution of 4.23 ml (5.12 g, 40 mmol, 1.1 equiv.) of 3-chloro-aniline in 15 ml of dry THF were added dropwise at 0° C. The reaction mixture was stirred for 5 min. at 0° C. and then allowed to warm up to room temperature. After stirring for 1 h at r.t., the dark brown suspension was filtered. The filtrate was concentrated in vaccuo, and the residue was dissolved in 200 ml of ethyl acetate, which was washed once with brine. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vaccuo. Concentration in vaccuo yielded 7.7 g of a dark brown residue which was purified by flash chromatography (heptane/ethyl acetate 4:1) to yield a the title compound as a white solid (total 5.05 g, 56%), MS (ISP): m/e=247.1, 249.1 (M+H+).

Provenance & Evidence