A common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, molecular formula is C8H10ClN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 32372-82-0.
1-Ethyl-3- (3-dimethylaminopropyl)carbodiimide (1.63 g, 8.54 mmol, 2.0 eq.) was added to a stirred solution of S14 (950 mg, 4.27 mmol, 1 eq.), isoindoline hydrochloride (731 mg, 4.70 mmol, 1.1 eq.), 1-hydroxybenzotriazole (635 mg, 4.70 mmol, 1.1 eq.) N-,N-diisopropylethylamine (3.26 mL, 18.8 mmol, 4.4 eq.) in dichloromethane 42 mL) at 0 C. The resulting solution was stirred at rt for 14 h before quenching with saturated sodium bicarbonate solution (30 mL). The organic layer was washed with 1 M hydrochloric acid solution (30 mL) and saturated sodium chloride solution (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (Si02, 3 : 10 hexanes/ethylacetate) to afford S15 (1.22 g, 91.8%) as a white amorphous solid. 1H NMR (400 MHz, CDC13) delta 10.47 (s, 1H), 7.48 – 7.21 (m, 5H), 7.15 (d, J= 7.4 Hz, 1H), 5.01 (s, 2H), 4.58 (s, 2H), 4.02 – 3.76 (m, 4H), 1.32 (d, J= 6.8 Hz, 7H).13C NMR (100 MHz, CDC13) delta 190.8, 167.6, 153.7, 144.9, 136.4, 136.4, 134.4, 132.5, 128.0, 127.7, 126.1, 123.3, 122.7, 111.2, 56.1, 53.4, 52.3, 27.3, 24.4 (2). HRMS (ESI+) m/z [M + Na+] calcd for C20H21NO3Na, 346.1419, found 346.1404.
The synthetic route of Isoindoline hydrochloride has been constantly updated, and we look forward to future research findings.
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