Glycine → 2-(5-nitro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid

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Reaction Steps

4-nitrophthalic anhydride (0.25 g, 0.0013 mol) and glycine (0.097 g, 0.0013 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.28 g (86%) 140 as very pale yellow crystals: mp=195–96° C.; Rf 0.79 (A): Rf 0.75 (B): Rf 0.28 (D): IR(cm−1): 2811–3150 (OH), 3115 (C═CH), 1787 (C═O), 1730 (bs, C═O), 1622 (C═C), 1551 (N═O), 1412 (C═C), 1391 (C—O), 1351 (N═O), 1117 (C—O), 720 (C—CH); MS m/z (rel intensity) 250 (7), 249 (62), 205 (100), 122 (10).

Provenance & Evidence