32372-82-0, 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.
Manganese dioxide (2.80 g, 24.0 mol, 10 eq.) was added to a solution of 93 (550 mg, 2.40 mmol, 1 eq.) in dichloromethane (120 mL) at room temperature. The resulting mixture was stirred at room temperature for 16 h, filtered through a small pad of celite, eluted with ethyl acetate, and concentrated. Solvent was removed to give the corresponding aldehyde, which was used further as obtained. Lithium hydroxide monohydrate (1.02 g, 24.0 mmol) was added to a solution of the aldehyde in methanol (8 mL), tetrahydrofuran (8 mL), and water (8 mL). The resulting mixture was stirred for 14 h at room temperature. The residue was treated with 1 M hydrochloric acid and the pH was adjusted to 2. The resulting suspension was extracted with ethyl acetate (3chi50 mL), and the combined organic layers were washed with saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford the corresponding acid as an off-white solid which was used further as obtained. 1-Ethyl- 3-(3- dimethylaminopropyl)carbodiimide (1.53 g, 4.80 mmol) was added to a stirred solution of the acid, isoindoline hydrochloride (485 mg, 3.12 mmol), 1-hydroxybenzotriazole (735 mg, 4.8 mmol), N,N-diisopropylethylamine (1.25 mL, 7.20 mmol) in dichloromethane (24 mL) at 0 C. The resulting solution was stirred at room temperature for 14 h before quenching with a saturated sodium bicarbonate solution (20 mL). The organic layer was washed with 1 M hydrochloric acid solution (15 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Si02, 1 :3 hexanes/ethyl acetate) to afford 94 as a light brown amorphous solid (331 mg, 43%). HRMS (ESI+) m/z [M + H+] calc. for C20H2oN03, 322.1443, found 322.1449.
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