Dimethyl(methylene)ammounium iodide → 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide

Participants

Reaction Conditions

Reaction Steps

Methyl indole-4-carboxylate (7.0 g, 40 mmol) and Eschenmoser's salt (N,N-dimethylmethyleneammonium iodide; 7.8 g, 42 mmol) are combined in 130 ml of acetic acid. After heating at 65° C. for 2 hours, the reaction mixture is concentrated in vacuo. The resulting solid is triturated with ethyl acetate, filtered and dried in vacuo to give 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide in quantitative yield.

Provenance & Evidence