Extracurricular laboratory: Synthetic route of C9H7NO3

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., Formula: C9H7NO3

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., Formula: C9H7NO3

Description 11:5-Methoxyindolin-2-oneTo 5-methoxyisatin (0.25 g, 1.41 mmol) in ethylene glycol (1 ml) was added hydrazine hydrate (~50%, 1.5 equiv., 0.14 ml) and potassium hydroxide (1 equiv., 79 mg). The reaction mixture was heated in microwave (150C, 5 min). Tic (EtOAc : hexane, 1:1) indicated the completion of the reaction. The reaction mixture was diluted with water, acidified to pH~1 with 2M HCI and extracted into ethyl acetate. The organic layer was dried (MgS04), filtered and volatiles were removed in vacuo. The residue was purified by ISCO Combiflash (100% DCM – 5% MeOH/DCM) to give the product as an off-white solid. The results set out below indicate the final product was the title compound D1 .1H NMR (CDCI3): 8.08 (1H, br s), 6.83 (1H, s), 6.77-6.71 (2H, m), 3.75 (3H, s), 3.50 (2H, s). 13C NMR (CDCI3): 176.3, 159.5, 135.7, 126.6, 112.5, 111.8, 109.8, 55.8, 36.5.MS: (MH+41) 205.0

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:
Patent; University of Greenwich; SPENCER, John; WO2012/25726; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem