cis-1,2,3,6-Tetrahydrophthalimide

pale yellow or light beige to yellow-brownish

30 g (0.20 mol) of phthalimide, 600 ml of N, N-dimethylformamide and 9 g of Raney nickel were placed in a 1 L stainless steel magnetic stirring autoclave, and the reaction kettle was closed.After the air in the autoclave was replaced with nitrogen, the stirring was started to increase.When the temperature rises to 110 ° C, the gauge pressure is 0 MPa.At this point, hydrogen is introduced and the temperature in the kettle is between 105 and 115 °C.After 70 minutes, The pointer of the pressure gauge is raised, the hydrogen inlet valve is closed, the stirring is continued for 30 minutes, and the pressure gauge is returned to zero. Add 30 g (0.20 mol) of phthalimide, 600 ml of N, N- in a 1 L stainless steel magnetic stirring autoclave.Dimethylformamide and 9 g of Raney nickel were used to seal the reaction vessel.After the air in the autoclave was replaced with nitrogen, the stirring was started to increase.When the temperature rises to 110 ° C, the gauge pressure is 0 MPa.At this point, hydrogen is introduced and the temperature in the kettle is between 105 and 115 °C.After 70 minutes, The pointer of the pressure gauge is raised, the hydrogen inlet valve is closed, the stirring is continued for 30 minutes, and the pressure gauge is returned to zero. In this way, whenever the pressure gauge is under pressure, the hydrogen flow is stopped. After the pressure gauge returns to zero, the hydrogen is re-passed. When the total reaction time reaches 10 hours, After cooling to 40 degrees, the liquid in the kettle was replaced with nitrogen, and the liquid reaction solution was poured out. Filtration, the catalyst was filtered off and the filtrate was transferred to a rotary evaporator.Vacuum was applied with a water vacuum pump, DMF was distilled under reduced pressure, and after 550 ml of distillate was distilled off, distillation was stopped. After cooling to room temperature, a large amount of white granular crystals were precipitated, filtered through a Buchner funnel, and the filtrate and the distillate were combined. The filter cake was washed with 20 ml of water. The filter cake was dried to obtain 30 g of pure white crystalline powder, and the melting range was 134.5 ° C - 135.4 ° C, and the liquid chromatographic analysis content was 99.51percent.The yield was 97.40percent based on phthalimide.General procedure: A mixture of a cyclic anhydride 1 (1 mmol), guanidiniumchloride (2) (1 mmol), Et3N (2 mmol) and FeCl3 (10 molpercent)in PEG-400 (0.5 mL) at 60°C for aromatic derivatives andat 100°C for aliphatic derivatives was stirred for an appropriatetime. The reaction progress was monitored by thinlayerchromatography. After the completion of the reaction, the reaction mixture was cooled to room temperature andthen was extracted with H2O and EtOAc. The organic layerwas dried over MgSO4 and then evaporated under reducedpressure. The residue was purified by column chromatographyon silica gel using n-hexane-EtOAc (7:3). The desired1H-isoindole-1, 3(2H)-diones were obtained in 70–95percentyields. Spectroscopy data for compounds 3 are in goodagreement with those previously reported.

Molecular Weight:151.16
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:151.063328530
Monoisotopic Mass:151.063328530
Topological Polar Surface Area:46.2
Heavy Atom Count:11
Complexity:221
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes