Hydrochloric Acid → Methyl 3-(2-cyano-5-dimethylaminomethylpyrrol-1-yl)benzoate

Participants

Reaction Steps

To the mixture of methyl 3-(2-dimethylaminomethyl-pyrrol-1-yl)benzoate (1.0 g) in dichloromethane (15 ml) was added 4N-hydrogen chloride in ethyl acetate solution (0.97 ml) under ice-cooling and the mixture was stirred for 5 minutes at the same temperature. To the mixture was added dropwise chlorosulfonyl isocyanate (0.4 ml) under ice-cooling and the mixture was stirred for 1 hour at the same temperature. To the mixture was added dropwise N,N-dimethylformamide (3.0 ml) under ice-cooling and the mixture was stirred for 1 hour at the same temperature. The reaction mixture was poured into a mixture of dichloromethane and water, and the separated aqueous layer was adjusted to pH 12 with 5N-sodium hydroxide solution. The aqueous layer was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give methyl 3-(2-cyano-5-dimethylaminomethylpyrrol-1-yl)benzoate (1.1 g) as an oil.

Provenance & Evidence