Electric Literature of 50727-04-3, 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. 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.
A mixture of 4-methoxyphthalic anhydride (27.8 g, 0.16 mol) and formamide (175 ml) was stirred and held at 2100C for 5 hours and was then allowed to cool to room temperature overnight. The solid material was filtered off, washed sequentially with water (100 ml), 50% aqueous acetone (50 ml) and diethyl ether (200 ml) and sucked dry under reduced pressure to afford A- methoxyphthalimide (21.3 g, 77%) as a pale yellow solid. 1H NMR (DMSOd6) 11.15 (1 H, br s), 7.74 (1 H, d), 7.33-7.28 (2H, m), 3.92 (3H, s). A stirred solution of 4-methoxyphthalimide (21.3 g, 0.12 mol) in anhydrous tetrahydrofuran (425 ml) at O0C was treated dropwise with a solution of borane in tetrahydrofuran (1M, 340 ml, 0.34 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to O0C, methanol (150 ml) was added dropwise followed by 5M hydrochloric acid (150 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo, the mixture was diluted with water (750 ml) and was extracted with dichloromethane (3 x 750 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3 x 750 ml) and the combined extracts were evaporated to dryness in vacuo to afford 5-methoxyisoindoline (8.34 g, 47%) as a brown oil. 1H NMR (DMSO-CJ6) 7.13 (1H, d), 6.84 (1H, d), 6.74 (1H, dd), 4.05 (2H1 s), 4.01 (2H, s), 3.73 (3H, s). MS: [M+H]+ 150.
The chemical industry reduces the impact on the environment during synthesis 5-Methoxyisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.
Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44054; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem