Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 39755-95-8, name is 5-Methoxyisatin, A new synthetic method of this compound is introduced below., Quality Control of 5-Methoxyisatin
A mixture of 5-methoxyisatin (2.84 g, 16 mmol) and K2CO3 (5.53 g, 40mmol) was dissolved in anhydrous DMF (12 mL) under Ar. Benzylbromide (5.71 mL, 48 mmol) was added dropwise and the mixturewas stirred at r.t. for 19 h. The mixture was extracted with dichloromethane (3 × 20 mL) and the organic phase was washed with H2O (20mL) and brine (20 mL), dried with MgSO4, filtered, and concentratedto obtain a red solid.14The crude material was dissolved in DMSO (12mL), hydrazine hydrate (1.81 mL, 32 mmol) was added dropwise andthe mixture was heated at 150 C for 5 h. The mixture was cooled tor.t., extracted with EtOAc (2 × 100 mL), and the organic phase waswashed with H2O (100 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (hexane/EtOAc) to give pure 1-benzyl-5-methoxy-2-oxindole (2.55 g, 63%) as a brown oil.15The above product was dissolved in acetic anhydride (11.5 mL, 121mmol) and DMAP (37 mg, 0.3 mmol) was added. The mixture was heated at reflux (140 C) for 6 h and then cooled to r.t. and evaporated under reduced pressure. The residue was dissolved in MeOH (40 mL)cooled at 0 C and then a solution of KOH (8.5 g, 151 mmol) in MeOH (60 mL) was added. The solution was stirred at r.t. for 18 h then the solution was cooled in an ice-bath at 0 C and 12 M aqueous HCl was added until pH 3. The organic solvent was evaporated under reduced pressure, H2O (50 mL) was added and the mixture was extracted with EtOAc (3 × 50 mL). The organic phase was dried over MgSO4, filtered,and concentrated. The residue was purified by flash chromatography(hexane/EtOAc) to give pure 2c.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Ortega-Martinez, Aitor; Molina, Cynthia; Moreno-Cabrerizo, Cristina; Sansano, Jose M.; Najera, Carmen; Synthesis; vol. 49; 23; (2017); p. 5203 – 5210;,
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