Ammonia → 4-(1-Amino-3-anilino-1,3-dioxopropan-2-yl)benzoic acid

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Reaction Steps

A solution of 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid (0.25 g, 0.67 mmol) in 7.0 N methanolic ammonia (1.9 mL, 13.4 mmol) in a sealed tube was heated to 160° C. for 1 hour in the microwave. The reaction was concentrated in vacuo and purified by reverse phase HPLC (15-75% MeCN/H2O with 0.05% TFA) to give the title compound as a white solid. 1H NMR (600 MHz, DMSO-d6) δ 12.90 (bs, 1H), 10.28 (s, 1H), 7.89 (d, J=8.5 Hz, 2H), 7.55 (m, 3H), 7.52 (d, J=8.5 Hz, 2H), 7.35 (bs, 1H), 7.27 (t, J=8.1 Hz, 2H), 7.03 (t, J=7.5 Hz, 1H), 4.66 (s, 1H); ESIMS calcd 299.0 (M++H), found 299.0 (M++H).

Provenance & Evidence