Application of 5394-18-3,Some common heterocyclic compound, 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, molecular formula is C12H12BrNO2, 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.
N-(4-Bromobutyl)phthalimide (1.5 g, 5.32 mmol) was suspendedin THF (48 mL) and treated with sodium iodide (0.80 g, 5.32 mmol), triethylamine (0.74 mL, 5.32 mmol) and morpholine (0.51 mL, 5.85 mmol). The mixture was then heated at reflux for 16 h. After cooling to ambient temperature, the solvent was removed in vacuo and the residue partitioned between H2O (100 mL) and CHCl3 (100 mL). The aqueous layer was further extracted with CHCl3 (100 mL) and the organic extracts combined, dried (MgSO4), filtered, filtered and the solvent removed under reduced pressure. The crude product was purified by flash chromatography on silica eluting with ethyl acetate to give phthalimide10 (1.02 g, 66%) as a pale yellow oil; numax/cm-12942, 2855, 2807, 1703, 1393, 1359, 1333, 1114, 1069, 1011, 862, 716, 528; deltaH (300 MHz; CDCl3) 7.86-7.77 (2 H, m), 7.73-7.67 (2 H, m), 3.69 (6 H, m), 2.40 (6 H, m), 1.71 (2 H, m), 1.50 (2 H, m); deltaC (75 MHz; CDCl3) 168.5, 134.0, 132.2, 123.3, 66.9, 58.4, 53.7, 37.9, 26.6, 23.8; m/z (+ESI) 289 ([M + H]+, 100); Found: M+, 289.15493. C16H20N2O3 requires 289.15467.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromobutyl)isoindoline-1,3-dione, its application will become more common.
Reference:
Article; Beinat, Corinne; Reekie, Tristan; Hibbs, David; Xie, Teresa; Olson, Thao T.; Xiao, Yingxian; Harvey, Andrew; O’Connor, Susan; Coles, Carolyn; Tsanaktsidis, John; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 200 – 205;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem