Gamma-Aminobutyric Acid → 4-(4-Nitro-1,3-dioxoisoindol-2-yl)butanoic acid

Participants

Reaction Steps

3-nitrophthalic anhydride (0.5 g, 0.0026 mol) and 4-aminobutyric acid (0.268 g, 0.0026 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.57 g (79%) 122 as a very pale orange powder: mp=144–146° C.; Rf 0.62 (A): Rf 0.87 (C): Rf 0.78(D): IR (cm−1): 3000–3250 (OH), 3219 (C═CH), 2953 (C—H), 1778 (C═O), 1716 (C═O), 1667 (C═O), 1615 (C═C), 1548 (N═O), 1442 (C═C), 1395 (C—O), 1355 (N═O), 1189 (C—O), 723 (C═CH); MS m/z (rel intensity) 313 (100), 278 (65), 277 (42), 191 (71).

Provenance & Evidence