Hydrochloric Acid → HCID 67228750, compound

Participants

Reaction Steps

4-(4-Dimethylaminomethyl-2-methoxyphenylamino)-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione (0.42 g, 1.0 mmol) was dissolved in 9:1 methylene chloride-methanol (75 mL) and a 2 M solution of hydrogen chloride in ether (1.0 mL) was added. The mixture was stirred at room temperature for 1 hour, and was evaporated under vacuum. The residue was triturated with ether and filtered, providing 0.44 g, in quantitative yield: mp>260° C.; 1H NMR (DMSO-d6) δ 1.96-2.14 (m, 1H), 2.53-2.68 (m, 8H), 2.84-2.95 (m, 1H), 3.90 (s, 3H), 4.24 (s, 2H), 5.13 (d, J=7.8 Hz, 1H), 7.13 (d, J=7.1 Hz, 1H), 7.28 (d, J=5.7 Hz, 1H), 7.25-7.66 (m, 4H), 8.41 (s, 1H), 11.11 (br, 1H), 11.14 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 31.0, 41.4, 48.8, 56.1, 59.4, 112.3, 113.7, 114.3, 119.3, 123.5, 126.1, 129.0, 132.2, 136.4, 141.7, 150.0, 167.0, 168.8, 170.0, 172.8; Anal. calcd for C23H25ClN4O5.0.5H2O.0.1Et2O: C, 57.44; H, 5.56; N, 11.45. Found: C, 57.44; H, 5.48; N, 11.08.

Provenance & Evidence