496-12-8, A common compound: 496-12-8, name is Isoindoline, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.
A 1.0 g (8.4 mmol) amount of isoindoline was dissolved in 25 mL of acetonitrile. After addition of potassium carbonate (2.3 g ,16.8 mmol), the resulting mixture was heated at 70 C. After 30 min, the solution was allowed to cool to room temperature. A 4.2 mL (47.2 mmol) amount of 1-bromo-3-chloropropane was added and the reaction mixture stirred at room temperature for 24 h. The solvent was removed under reduced pressure and 60 mL water added to the residue. The product was extracted with 3×30 mL dichloromethane. The combined organic fractions were washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure. Purification by column chromatography (DCM:MeOH(NH3), 99:1 (v/v)) was performed and enabled collection of the product as a brown liquid (1.27 g,77%). TLC: Rf 0.7 (DCM:MeOH(NH3), 9:1, v/v). 1H NMR (300 MHz,CDCl3) delta: 7.21 (s, 4H, Haro); 3.95 (s, 4H, 2 CH2); 3.69 (t, J 6.8 Hz, 2H,CH2); 2.90 (t, J 7.1 Hz, 2H, CH2); 2.07 (p, J 7.0 Hz, 2H, CH2). 13C NMR (75 MHz, CDCl3) delta: 140.0 (2 Caro); 126.7 (2 Caro); 122.3 (2 Caro); 59.1 (2 CH2); 53.0 (CH2); 43.1 (CH2); 31.9 (CH2). LCMS (ESI+): Calc.for [M+H]: 196.05; 198.07. Found: 195.95; 197.91.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Isoindoline, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Donnier-Marechal, Marion; Larchanche, Paul-Emmanuel; Le Broc, Delphine; Furman, Christophe; Carato, Pascal; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 89; (2015); p. 198 – 206;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem