N,N-Dimethylaniline → HCID 86603517, compound

Participants

Reaction Steps

Hexanoic acid, 2-chlorocarbonyl-4-methyl-3-oxo-1-phenyl-pyrazolidin-4-ylmethyl ester (0.80 g, 0.0022 mol) was dissolved in tetrahydrofuran (10 ml) and added to a stirred solution of 2-methylamino-benzoic acid, 3-(2-dodecyloxy-5-methyl-phenylcarbamoyl)-4-hydroxy-naphthalen-1-yl ester [A] (1.28 g, 0.0021 mol) and N,N-dimethylaniline (0.28 g, 0.0023 mol) in dry tetrahydrofuran (5 ml) and the solution stirred for 72 hr under argon atmosphere in a flask equipped with a reflux condenser to limit evaporation. The reaction mixture was evaporated, re-dissolved in ethyl acetate (300 ml) and washed with 2 M aqueous hydrochloric acid (150 ml) followed by water (20 ml). The organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated to give a yellow-brown oil which contained product and starting amine. The oil was chromatographed on a Flashpak Si 50 g column eluting with hexane/ethyl acetate (4:1->2:1). The higher running components were discarded. The more polar component was evaporated to give pale yellow viscous oil. Analysis was consistent with the desired product. The total yield of product was 1.3 g (62%).

Provenance & Evidence