Research on new synthetic routes about 2-(3-Oxobutyl)isoindoline-1,3-dione

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference of 3783-77-5, A common heterocyclic compound, 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, molecular formula is C12H11NO3, its 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.

(1) Synthesis of N-[3-(N-hydroxyimino)butyl]-phthalimide 1.08 g (5.00 mmol) of N-(3-oxobutyl)phthalimide was dissolved in 10 ml of methanol and to the solution was added 0.695 g (10.0 mmol) of hydroxylamine hydrochloride. To this suspension was added 2 ml of 5N aqueous sodium hydroxide solution, followed by being stirred at room temperature for 16 hours. The reaction mixture was poured into 100 ml of saturated aqueous sodium hydrogencarbonate and extracted with chloroform (30 ml*3), and the combined organic layer was dried over magnesium sulfate. Chloroform was distilled off and the residual solids were washed with hexane to give 0.98 g (yield 84%) of the titled compound as colorless crystals. Melting point 151-172 C., 1 H-NMR spectrum (DMSO-d6, TMS as internal standard); delta=1.81(s, 3H*0.75), 1.83(s, 3H*0.25), 2.3-2.6(m, 2H), 3.78(t, J=6 Hz, 2H*0.75), 3.91(t, J=6 Hz, 2H*0.25), 7.85(s, 4H), 10.15(bs, 1H*0.75), 10.34(s, 1H*0.25)ppm,

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.