3-(4-NITRO-1,3-DIOXO-1,3-DIHYDRO-ISOINDOL-2-YL)-PROPIONIC ACID synthesis

Yield:15728-05-9 0.55 g (80%)

Steps:

3-nitro-N-(2-carboxyethyl)phthalimide (121)

3-nitro-N-(2-carboxyethyl)phthalimide (121) 3-nitrophthalic anhydride (0.5 g, 0.0026 mol) and β-alanine (0.23 g, 0.0026 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.55 g (80%) 121 as a pale yellow powder: mp=146-148° C.; R_f0.73 (A): R_f0.87 (C): R_f0.57 (D): ¹H NMR (DMSO-d₆) δ2.60 (t, J=7.4 Hz, 2H), 3.78 (t, J=7.4 Hz, 2H), 8.07 (dd, J=7.5, 8.0 Hz, 1H), 8.16 (d, J=7.5 Hz, 1H), 8.27 (d, J=8.0, 1H); IR (cm^-1): 2800-3200 (OH), 3097 (C=CH), 2620 (C-H), 1781 (C=O), 1725 (bs, C=O), 1617 (C=C), 1545 (N=O), 1468 (C=C), 1450 (C=C), 1395 (C-O), 1360 (N=O), 1235 (C-O), 723 (C=CH); MS m/z (rel intensity) 264 (76), 263 (100), 191 (90).

References:

US6468990,2002,B1