Introduction of a new synthetic route about Isoindoline hydrochloride

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 32372-82-0, name is Isoindoline hydrochloride, A new synthetic method of this compound is introduced below., 32372-82-0

1-Ethyl-3-(3- dimethylaminopropyl)carbodiimide (2 eq.) was added to a stirred solution of 7 (1 eq.), isoindoline hydrochloride (1.5 eq.), 1-hydroxybenzotriazole (2 eq.) N,N- diisopropylethylamine (2 eq.) in dichloromethane (150 mL) at 0 C. The resulting solution was stirred at room temperature for 14 h before quenching with saturated sodium bicarbonate solution (120 mL). The organic layer was washed with 1 M hydrochloric acid solution (120 mL) and saturated sodium chloride solution (120 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Si02, 1 :4 hexanes/ethyl acetate) to afford 8 (82%) as a white amorphous solid. 1H- NMR (400 MHz, CDC13) delta 7.97 (m, 1H), 7.43 (m, 2H), 7.37 (m, 2H), 6.07 (s, 2H), 6.00 (s, 2H), 4.52 (s, 2H), 4.41 (s, 2H), 3.35 (s, 3H), 3.27 (s, 3H), 3.05 (m, 1H), 1.14 (d, J=7.52, 6H).13C- NMR (100 MHz, CDC13) delta 169.5,157.5, 156.6, 140.0 (2), 130.6, 128.5 (2), 126.2 (2), 126.0, 111.2, 99.9, 95.2, 94.5, 56.1, 55.6 (2), 26.9, 23.6 (2).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem