Extracurricular laboratory: Synthetic route of C8H6N2O2

Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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. Product Details of 3676-85-5

Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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. Product Details of 3676-85-5

1.00 mmol of 5-aminoisoindoline-1 ,3-dione, commercial product, was solubilized in 1.0 mL of toluene and added with 1.20 mmol of commercial benzoylchloride and 1.20 mmol of triethylamine, then heated under reflux for 6 hours. After cooling, the solid that separates was collected by filtration, then dried under vacuum and purified by crystallization in ethanol. 250.3 mg of the desired product of the title were so obtained (yield 94%). It was characterized by chemical-physical and spectroscopical data. (0165) M.p. (C): >300. 1 H-NMR (delta, DMSO, d6): 7.649 (t, 1 H, Ar, J=7.25), 7.825 (t, 2H, Ar, J=7.69), 7.825 (d, 2H, Ar, J=8.32), 7.993 (d, 1 H, Ar, J=7.04), 8.145 (dd, 1 H, Ar, J=7.76, J=1.722), 8.331 (s, 1 H, Ar), 10.792 (s, 1 H, NH, exc), 11.269 (s, 1 H, NH, exc).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3676-85-5, its application will become more common.

Reference:
Patent; UNIVERSITA’ DI PISA; PAOLINI, Edoardo; QUATTRINI, Luca; COVIELLO, Vito; ANTONIOLI, Luca; FORNAI, Matteo; BLANDIZZI, Corrado; OH, Won Keun; LA MOTTA, Concettina; (30 pag.)WO2018/189679; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem