Reference of 59-48-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 59-48-3 as follows.
To 5 L 4-neck flask (equipped with a mechanical stirrer, condenser and N2 inlet) was charged with 2 L water and 50% sodium hydroxide (NAOH) (2.52 mol, 201.6 g, 2.25 equiv) followed by oxindol (1.12 mol, 150 g, 1 equiv) and the reaction mixture was heated TO-40 C. Dimethylsulfate (1.68 mol, 211.7 g (159 mL), 1.5 equiv) was added slowly via syringe. The addition was slightly exothermic with temperature rising to 53 C. When addition was complete, the reaction mixture was heated to- 100 C and held for 15 minutes (min). The reaction mixture was cooled TO-600 C, and a second portion of dimethylsulfate (0.476 mol, 60 g (45 mL), 0.425 equiv) was added. The reaction mixture was heated TO ~ 100 C and held 15 min. TLC (heptane/ethyl acetate (EtOAc), 1: 1) show methylation was essentially complete. The reaction mixture was cooled TO-50 C and the pH adjusted to-7 with concentrated HCI. The reaction mixture was seeded, cooled to room temperature and allowed to stand overnight. The solids were collected, wash with water (4X) and dried overnight in a vacuum over AT-40 C to give 110.7 g (67%) of 1-methyl-1, 3-dihydroindol-2-one as a pink solid, mp 84-86 C.
According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.
Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/37820; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem