Dimethylamine → HCID 10823474, compound

Participants

Reaction Steps

100 g of methyl indole-4-carboxylate were dissolved in 500 ml of glacial acetic acid. To the solution were added dropwise at room temperature a mixture of 86 ml of a 40% strength aqueous dimethylamine solution, 55 ml of a 37% strength aqueous formaldehyde solution and 250 ml of glacial acetic acid. The reaction mixture was subsequently stirred at room temperature for 20 hours. To work up the reaction mixture it was cooled in ice and 20% strength aqueous sodium hydroxide solution was added until pH 9 was reached. This was followed by extraction three times with dichloromethane, and the combined organic extracts were dried with sodium sulfate, filtered and concentrated. 127 g of crude methyl 3-dimethylaminomethylindole-4-carboxylate were obtained as a pale yellow oil.

Provenance & Evidence