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ChemicalBook CAS DataBase List 1-benzyl-1H-indole-5-carbonitrile
80531-13-1

1-benzyl-1H-indole-5-carbonitrile synthesis

9synthesis methods
-

Yield:80531-13-1 65%

Reaction Conditions:

with propylsulfonic acid-functionalized silica in toluene;Reflux;

Steps:

3.2 General procedure for the synthesis of N-benzyl 2,3-unsubstituted indoles

General procedure: A 25 mL round-bottomed flask was charged with N-benzyl N-(2,2-diethoxyethyl)anilines (2 mmol), MCM-41-SO3H (0.10 g), and toluene (10 mL). The mixture was stirred under refluxing condition for several hours until the reaction was completed based on GC determination. After the reaction was finished, the mixture was cooled to room temperature. Then the catalyst MCM-41-SO3H was filtered off, and washed with toluene (10 mL×3). The combined filtrate was concentrated in vacuo to remove the solvent. The resulting residue was purified by flash column chromatography on basic Al2O3 (petroleum ether/ethyl acetate) to afford the desired N-benzyl 2,3-unsubstituted indoles.

References:

Sun, Nan;Hong, Lingfen;Huang, Fang;Ren, Hong;Mo, Weimin;Hu, Baoxiang;Shen, Zhenlu;Hu, Xinquan [Tetrahedron,2013,vol. 69,# 19,p. 3927 - 3933]