Formic Acid → N-[5-chloro-2-(methylphenylamino)phenyl]formamide

Participants

Reaction Steps

4-Chloro-N1-methyl-N1-phenylbenzene-1,2-diamine (9.3 g, 40.1 mmol) was dissolved in formic acid (60 mL) and heated to reflux. After 2 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (500 mL) and washed with aq. NaHCO3 (5%, 500 mL). The organic layer was dried, filtered and concentrated under reduced pressure. The residual oil was chromatographed over silica (cyclohexane/CH2Cl2, 9/1, v/v) to give pure title compound (10.4 g, 100% yield). Data: Rf 0.25 (heptane/ethyl acetate, 3/1, v/v). (m/z)=261 (M+H)+.

Provenance & Evidence