Hydrochloric Acid → N-ethyl-1,2,3,4-tetrahydrocarbazole-6-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

1,2,3,4-Tetrahydrocarbazole-6-carboxylic acid methyl ester (460 mg) prepared by the method described in Journal of Chemical Society, p.809 (1926) was dissolved in 2.5 mL of DMF, and the solution was added with 0.3 mL of ethyl iodide and 120 mg of sodium hydride and stirred at room temperature at 50° C. for 2 hours under a nitrogen flow. Then, the reaction mixture was added with water, neutralized with 2 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: dichloromethane) to obtain 490 mg of N-ethyl-1,2,3,4-tetrahydrocarbazole-6-carboxylic acid methyl ester.

Provenance & Evidence