Electric Literature of 14192-26-8, A common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, molecular formula is C10H9NO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a stirred solution of methyl 2-oxoindoline-6-carboxylate (10.0 g, 52.33 mmol) in 1,4-dioxane (500 mL) was added selenium dioxide (27.9 g, 261.68 mmol) and the resulting reaction mixture was stirred vigorously at 100 C for 1 h. After completion of the reaction, the reaction mixture was diluted with EtOAc and water and filtered through a bed of celite. The filtrate layers were separated and the organic layer was washed with water and brine, dried over anhydrous Na2S04 and then evaporated under reduced pressure to provide the crude product. This was purified by Comb1-flash using 50% EtOAc in hexanes as eluent to afford methyl 2,3-dioxoindoline-6-carboxylate (3.5 g, 17.06 mmol, 34% yield) as a light yellow solid.
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; CURADEV PHARMA LIMITED; BANERJEE, Monali; MIDDYA, Sandip; BASU, Sourav; YADAV, Dharmendra; GHOSH, Rajib; PRYDE, David; SHRIVASTAVA, Ritesh; SURYA, Arjun; (190 pag.)WO2018/234807; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem