6-Aminohexanoic Acid → 6-(4-Nitro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)hexanoic acid

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Reaction Steps

3-nitrophthalic anhydride (0.5 g, 0.0026 mol) and 6-aminohexanoic acid (0.34 g, 0.0026 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.75 g (95%) 124 as a pale yellow powder: mp=144° C.; Rf0.68 (A): Rf0.89 (C): Rf0.71 (D): IR (cm−1): 2800-3180 (OH), 3096 (C═CH), 2620 (C—H), 1777 (C═O), 1723 (bs, C═O), 1617 (C═C), 1543 (N═O), 1468 (C═C), 1442 (C═C), 1395 (C—O), 1359 (N═O), 1057 (C—O), 723 (C═CH); MS m/z (rel intensity) 305 (100), 191 (17).

Provenance & Evidence