Analyzing the synthesis route of C8H6N2O2

Reference of 3676-85-5, A common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

Reference of 3676-85-5, A common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

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 4- chlorobenzoylchloride and 1.20 mmol of triethylamine, then heated at reflux for 10 hours. After cooling, the solid that separates was collected by filtration, dried under vacuum and purified by crystallization in methanol. 285.5 mg of the desired product of the title were so obtained (yield 95%). It was characterized by chemical-physical and spectroscopical data. M.p. (C): >300. 1 H-NMR (delta, DMSO, d6): 8.318 (d, 1 H, Ar, J=1.64), 8.131 (dd, 1 H, Ar, J=8.24, J=1.84), 8.024 (d, 2H, Ar, J=8.60), 7.838 (d, 1 H, Ar, J=8.16), 7.659 (d, 2H, Ar, J=8.61), 10.844 (s, 1 H, NH, exc), 1 1.272 (s, 1 H, NH, exc).

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; 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