4-Aminobenzoic Acid → 4-(2-Oxopyrrolidin-1-yl)benzoic acid

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Reaction Steps

A solution of 4-aminobenzoic acid (Aldrich, 3.0 g, 21.9 mmol) and ethyl 4-bromobutyrate (Aldrich, 6.4 g, 32.8 mmol) in 20 mL of dimethylformamide was stirred at reflux for 24 h. The solvent was removed under vacuum to give a crude solid which was suspended in 15 mL of water, collected by filtration and dried. The solid was suspended in a small amount of ether (5 mL), filtered and dried to give 3.0 g (66%) of the title compound as a white solid, mp 244-246° C. (ether/ethanol), lit.mp 244-245° C. [Hopff et al. Ger. 859, 007, Sep. 22, 1952; Chem. Abstr. 52 11124h (1958)].

Provenance & Evidence