3-Aminobenzoic Acid → 2-(3-Carboxyphenyl)-1,3-dioxoisoindoline-5-carboxylic acid

Participants

Reaction Steps

4-carboxyphthalic anhydride (1.0 g, 0.0052 mol) and m-aminobenzoic acid (0.714 g, 0.0052 mol) were refluxed as above overnight. Crystallisation of the product from MeOH yielded 1.21 g (72%) of 106 as a white solid: mp=>380° C.; Rf 0.87 (A): Rf 0.75 (C): Rf 0.27 (D):IR (cm−1): 2700–3125 (OH), 3090 (C═CH), 2665 (C—H), 1780 (C═O), 1731 (C═O), 1699 (C═O), 1610 (C═C), 1589 (C═C), 1484 (C═C), 1452 (C═C), 1383 (C—O), 1310 (C—O), 1222 (C—O), 722 (C═CH); MS m/z (rel intensity) 311 (22), 310 (100).

Provenance & Evidence