Reference of 550-44-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 550-44-7, name is 2-Methylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.
General procedure: To a solution of magnesium (1.0 M in THF, 22 mL, 23.8 mmmol) was added 4-bromo-1-butene (2.2mL, 22 mmol) under a nitrogen atmosphere. After stirring the mixture for 30 min, the resultingsolution was added to the solution of N-methylphthalimide (1.42 g, 6.38 mmol) in THF (34 mL) at-20 C and stirred for additional 1 hour at the same temperature. The reaction was quenched byaddition of saturated aqueous NH4Cl (20 mL), and the resulting solution was extracted with EtOAc(30 mL). The organic extracts were washed with brine (20 mL), dried over Na2SO4, filtered, andconcentrated in vacuo to give a crude material (1.61 g). To a solution of the crude material (1.61 g) in dichloromethane (68 mL) was added triethylsilane (4.3mL, 27 mmmol) and boron trifluoride diethyl ether complex (3.4 mL, 27 mmol) under a nitrogenatmosphere at -20 C. The mixture was allowed to warm to 0 C and stirred for 30 min. The reactionwas quenched by addition of saturated aqueous NaHCO3 (50 mL). The resulting solution wasextracted with EtOAc (60 mL). The organic extracts were washed with brine (50 mL), dried overNa2SO4, filtered, and concentrated in vacuo to give a crude material. This material was purified bycolumn chromatography (silica gel, hexane/EtOAc = 3/1 to 1/1) to give 3a (1.17 g, 5.81 mmol, 85%for 2 steps) as a pale yellow oil. Rf = 0.32 (silica gel, hexane/EtOAc = 1/1); 1H NMR (300 MHz, CDCl3) delta 7.83 (d, J = 6.6 Hz, 1H, ArH), 7.56-7.41 (m, 3H, ArH), 5.70 (ddt, J = 6.3, 10.5, 17.1 Hz, 1H, CH),4.97-4.90 (m, 2H, CH2), 4.53 (t, J = 4.2 Hz, 1H, CH), 3.11 (s, 3H, CH3), 2.13-2.00 (m, 2H, CH2), 1.80 (m, 1H,CH2), 1.60 (m, 2H, CH2); 13C NMR (75 MHz, CDCl3) delta 168.5 (C), 144.6 (C), 137.1 (CH), 132.7 (C),131.2 (CH), 128.0 (CH), 123.4 (CH), 121.9 (CH), 115.1 (CH2), 60.9 (CH), 29.7 (CH2), 27.2 (CH3),26.6 (CH2).
The synthetic route of 2-Methylisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.
Reference:
Article; Sengoku, Tetsuya; Nagai, Yuichiro; Inuzuka, Toshiyasu; Yoda, Hidemi; Synlett; vol. 30; 2; (2019); p. 199 – 202;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem