Extracurricular laboratory: Synthetic route of 496-12-8

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

Electric Literature of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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.

To a stirred solution of isoindoline (2 g, 16.8 mmol) at 0 0C5 was added slowly concentrated H2SO4 (10 mL). Then a mixture of 70% HNO3 (2.1 mL, 33.6 mmol) and concentrated H2SO4 (2 mL) was added. After addition the mixture was stirred at 00C for 30 min. The reaction mixture was poured into ice water. The mixture was carefully neutralized with 50% aq. NaOH to pH 10 and extracted with EtOAc (3 x). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 5-nitroisoindoline as a brown solid. LCMS calc. = 165.1; found = 164.9 (M+H)+. 1H NMR (500 MHz5 CDCl3): delta 8.11 (d, J= 8.0 Hz, 2 H); 7.39 (d, J= 7.8 Hz, 1 H); 4.33 (s, 4 H); 2.31 (br s, 1 H).

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

Reference:
Patent; MERCK & CO., INC.; WO2007/81569; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem