Reaction Steps
4-Methoxy-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione was prepared by the procedure of Example 1 from 3-methoxyphthalic anhydride (1.0 g, 5.6 mmol) {Rao. A. V. R. et al, Indian J. Chem. 1981, 20 (B), 248}, 3-aminopiperidine-2,6-dione hydrogen chloride (0.92 g, 5.6 mmol) and sodium acetate (0.48 g, 6.0 mmol) in acetic acid (20 mL). The product was a white solid (0.44 g, 27% yield); mp, 281.5-282.5° C.; 1H NMR (DMSO-d6) δ2.00-2.08 (m, 1H, CHH), 2.56-2.62 (m, 2H, CH2), 2.82-2.91 (m, 1H, CHH), 3.97 (s, 3H, CH3), 5.08 (dd, J=5.3, 12.8 Hz, 1H, NCH), 7.46 (d, J=7.2 Hz, 1H, Ar), 7.52 (d, J=8.5 Hz, 1H, Ar), 7.84 (d, J=7.8 Hz, 1H, Ar), 11.10 (br s, 1H, NH); 13C NMR (DMSO-d6) δ21.97, 30.92, 48.73, 56.33, 115.24, 116.11, 119.01, 133.19, 137.15, 156.49, 165.37, 166.84, 169.94, 172.79; Anal Calcd for C14H12N2O5: C, 58.33; H, 4.20; N, 9.72. Found: C, 58.23; H, 3.90; N, 9.53.
