Methyl 4-Formylbenzoate → HCID 24827971, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-formylbenzoate (5.0 g, 0.03 mol) and N-methyl-1,2-phenylene diamine (3.7 g, 0.03 mol) in nitrobenzene was heated at 140-150° C. overnight, cooled to room temperature, filtered and the filtercake washed with hexane. The combined filtrates were evaporated to dryness under reduced pressure. The resultant residue was purified by flash chromatography (silica, CHCl3:MeOH 95:5) to afford the title compound in 65% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, CDCl3): 8.2 (d, J=8 Hz, 2H), 7.88 (d, J=8 Hz, 2H), 7.83 (s, 1H), 7.37 (m, 1H), 7.35 (m, 2H), 3.96 (s, 3H), 3.9 (s, 3H). LCMS (ESI+) 267 (MH+).

Provenance & Evidence