Extracurricular laboratory: Synthetic route of 480-91-1

Electric Literature of 480-91-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 480-91-1, name is Isoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

Electric Literature of 480-91-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 480-91-1, name is Isoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of sodium hydride (450.6 mg, 11.26 mmol), freshly washed with hexane and suspended indry THF, was added a solution of isoindolin-1-one (1.00 g, 7.51 mmol) in tetrahydrofuran (25 mL) at 0 Cunder a nitrogen atmosphere. The reaction mixture was stirred (30 min) before tert-butyl bromoacetate(1.664 mL, 11.26 mmol) was added slowly. The reaction mixture was stirred (16 h) at room temperature.The reaction mixture was quenched with methanol (5 mL). The solvent was removed under vacuum andthe resulting crude residue submitted to column chromatography (hexane/ethyl acetate, 4:1) to givepure tert-butyl 2-(1-oxoisoindolin-2-yl)acetate 1 as an off-white solid (1.802 g, 97%); mp = 62-64 C; Rf =0.33 (ethyl acetate/hexanes, 2:1); FT-IR (neat): 2972, 2932, 1738, 1687 cm -1; 1H NMR (400 MHz, CDCl3):delta 7.86 (d, J = 7.6 Hz, 1H), 7.54-7.52 (m, 1H), 7.47-7.43 (m, 2H), 4.51 (s, 2H), 4.29 (s, 2H), 1.46 (s, 9H). 13CNMR (100 MHz, CDCl3): delta 168.8, 168.1, 141.6, 131.9, 131.6, 127.9, 123.9, 122.7, 82.2, 50.5, 44.5, 28.0.ppm; LRMS calcd for C14H17NO3 (M+H) 248, found 248.

The chemical industry reduces the impact on the environment during synthesis Isoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Patil, Pravin C.; Luzzio, Frederick A.; Synlett; vol. 28; 14; (2017); p. 1729 – 1732;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem