Application 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.
Potassium hydroxide (0.415 g, 7.4 mmol) was added to a solution of 4-aminophthalimide (35) (1.00 g, 6.17 mmol) in dimethylformamide (50 ml) and the mixture was stirred at ambient temperature. After 2 hours, 4-trifluoromethylbenzylbromide (36) (1.9 mL, 12.34 mmol) was further added to the mixture and the mixture was stirred for another 18 hours. Water (100 ml) and ethyl acetate (100 ml) was added and the resulting phases separated. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuum. Purification by chromatography on silica gel (Gradient: 0-50 % ethyl acetate in cyclohexane) afforded Compound 37 as a yellow solid (0.750 g, 38 % yield): Rf= 0.2 (hexane/ethyl acetate 2:1 v/v). The Compound 37 (0.20g, 0.62 mmol.) was dissolved in dichloromethane (5 ml) and purged with argon. Benzyl chloroformate (0. lmL, 0.74 mmol) and triethylamine (0.60 mmol) were added to the amine solution and the resulting mixture was stirred for 2 hours at ambient temperature. After removal of the dichloromethane in vacuum, ethyl acetate (20 ml) and 10 % citric acid (20 ml) were added thereto and the resulting phases were separated. The organic phase was washed with 10 % sodium bicarbonate (20 ml) and brine (20 ml), dried over sodium sulfate and concentrated in vacuum. The residue was purified by chromatography on silica gel, and the resulting product was Compound 38. Compound 38,
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.
Reference:
Patent; TAIWANJ PHARMACEUTICALS CO., LTD.; YANG, Syaulan S.; LEE, Kuang Yuan; LIU, Meng Hsien; JIANG, Yan-Feng; FAN, Yu-Shiou; CHEN, Chi-Han; LIU, Sheng Hung; (94 pag.)WO2019/51222; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem