Hydrochloric Acid → 2-(3-hydroxy-4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)isoindoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-hydroxy-4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butylcarbamoyl)benzoic acid (2.56 g, 5.62 mmol) and hydrogen chloride in dioxane (42.2 mL, 169 mmol) was heated at 100° C. for 45 min. The reaction was cooled to rt, and then extracted with EtOAc. The combined organic layers were concentrated to get 2-(3-hydroxy-4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)isoindoline-1,3-dione which was used as-is in the next step. LC-MS (M+H)+=438.2. 1H NMR (500 MHz, methanol-d4) δ 9.26 (s, 1H), 8.13-7.97 (m, 3H), 7.87-7.83 (m, 2H), 7.83-7.77 (m, 2H), 4.36 (dd, J=9.9, 3.5 Hz, 1H), 4.27 (dd, J=9.8, 6.1 Hz, 1H), 4.12 (dt, J=6.0, 2.9 Hz, 1H), 3.95-3.81 (m, 2H), 2.48 (s, 3H), 2.08-1.87 (m, 2H).

Provenance & Evidence