4-Bromophthalimide

yellow to slight yellow powder

A mixture of intermediate I-54 (6.6 g, 0.30 mol, 1.0 eq) and formamide (10 mL, 2.4 mol, 8.0 eq) was stirred at 200° C. for 2 hours and poured onto a mixture of ice and water. The resulting crystals were collected by filtration and dried in vacuo to give intermediate I-55 (7.0 g, 99percent). MS (ESI): m/z 227 (M+HCompound E-1 (110 mmmol) was refluxed in formamide for 4 hours to obtain compound E-2 (103 mmol, 94percent).Compound E-2 (100 mmol) was reacted in 28percent ammonia solution at room temperature for 24 hours to obtain compound E-3 (74 mmol, 74percent).Compound E-3 (70 mmol) was dissolved in DMF, The mixture was allowed to react with thionyl chloride in an ice bath for 24 hours to obtain compound E-4 (53 mmol, 75percent).A mixture of 5-bromoisobenzofuran-l, 3-dione (6.6 g, 29.1 mmol) and formamide (10 mL, 252 mmol) was heated at 200 °C for 2 h. Then the reaction was cooled to rt and poured into H5-bromoisobenzofuran-1, 3-dione (6.6 g, 29.1 mmol) andFormamide (10 mL, 252 mmol)The mixture was heated to 200 ° C and stirred for 2 hours.Cool to room temperature and pour into water. The collected solid was washed with methanol (10 mL), dried in vacuo, The title compound was obtained as an orange solid (5.6 g, 85percent).A mixture of 5-bromoisobenzofuran- 1, 3-dione (2) (13.2 g, 58.1 mmol) and formamide (20 mL) was stirred at 200 °C for 2 h. After cooling to room temperature, the reaction mixture was poured into water and stirred for 1.5 h. The mixture was filtered and the solid was dried to give 5-bromoisoindoline-1, 3-dione (3) (11 g, 81 percent yield).1H- NMR (400 MHz, CDC13) 11.44 (s, 1H), 7.95-7.99 (m, 2H), 7.70-7.72 (m, 1H).No. I.1-117: 3-Acetyl-7-bromo-4-hydroxyisoquinolin-1(2H)-one 5-Bromophthalic acid (116 g, 473 mmol) was added to acetic anhydride (300 mL), heated to 130-135 ° C and reacted under reflux for 2 h.The resulting oily substance was evaporated to dryness under reduced pressure and the temperature was slowly lowered to 20 ° C to precipitate a yellow solid. Stirring was continued for 30 min at 20 ° C, suction filtered and rinsed with n-heptane (120 mL)Compaction, pumping to no droplets.Solid 5-bromophthalic anhydride was transferred to a flask, Under mechanical stirring, urea (49.8 g, 826 mmol) was added and the mixture was heated to 110-120 ° C and stirred for 6 h.Cooled to 70 , add 95percent ethanol (1000ml), heated to 75-85 , stirred for 2h, slowly cooled to 30 , stirred for 1h, and then slowly cooled to 0-5 for 1h, Filtered by suction, rinsed with ice-ethanol (120 ml) and dried in vacuo at 70 ° C gave a pale yellow 5-bromophthalimide (65.6 g, 61.3percent yield).4-Bromophthalic anhydride (2.26 g, 0.01 mol) was added to urea (6.0 g, 0.1 mol). General procedure: 0.01g of MnO2 catalyst, 0.5mmol of 1-indanone, 0.2g of ammonia water (25wtpercent) and 2g of chlorobenzene were added to a stainless steel autoclave with a polytetrafluoroethylene inner liner.The temperature was raised to 110 by automatic temperature controller, 0.6MPa oxygen was added and the reaction was continued for 4h. The pressure was kept constant during the reaction.The reaction product was analyzed using GC-MS with a phthalamide yield of 85percent.Synthesis of Exemplified Compound 31 (A) Synthesis of Compound 31-a 700 g of monosodium 4-bromophthalate, 590 g of formamide, 89 ml of concentrated sulfuric acid, and 360 ml of diglyme were placed into a 3 L three-necked flask, and the mixture was stirred under heating at an inside temperature of 130 to 140 C. for 7 hours. After cooling of the mixture to room temperature, 930 ml of DMF and 460 ml of water were added thereto, and the mixture was stirred at room temperature for 2 hours. Crystals were collected through filtration and added to 1.5 L of isopropyl alcohol. The resultant was refluxed under heating for 30 minutes, and then stirred at room temperature for 3 hours. The crystals were collected through filtration, washed with running hexane, and dried, to thereby obtain 563 g (95percent yield) of Compound 31-a.To a stirred solution of 5-amino-1H-isoindole-1, 3(2H)-dione (1.0 g, 6.2 mmol) dissolved in sulfuric acid solution (2 mL of Con.

Molecular Weight:226.03
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:224.94254
Monoisotopic Mass:224.94254
Topological Polar Surface Area:46.2
Heavy Atom Count:12
Complexity:241
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes