Extracurricular laboratory: Synthetic route of 21857-45-4

Related Products of 21857-45-4, A common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, molecular formula is C9H11NO, 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.

Related Products of 21857-45-4, A common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, molecular formula is C9H11NO, 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 100 mL round- bottomed flask, flushed with nitrogen, were added 17 (91 mg, 0.5 mmol), 5-methoxyindoline (82 mg, 0.55 mmol), BuOH (10 mL), and 2-3 drops of cone. HC1. The reaction mixture was heated at reflux with stirring for 12 h until the starting material 17 disappeared (TLC). The reaction solution was allowed to cool to room temperature; the solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel with hexane: acetyl acetate = 20: 1 as the eluent. Fractions containing the product (TLC) were combined and evaporated to afford 93 mg (63%) 8 as a white powder: mp 201.1-202.3 C; Rf 0.5 (AcOEt/Hexane 3 : 1); 1H NMR (DMSO-d6) delta 2.42 (s, 3 H), 2.53 (s, 3 H), 3.25 (t, 2 H), 3.75 (s, 3 H), 4.39 (t, 2 H), 6.79 (t, 2 H), 6.89 (d, 1 H), 8.48 (d, 1 H), Anal. Ci7H17N302

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; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (111 pag.)WO2016/100495; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem