4-Butylaniline → HCID 2735693, compound

Participants

Reaction Steps

To 300 ml of concentrated hydrochloric acid was added a solution of 4-n-butylaniline (20.0 g, 134.2 mmole) in 200 ml 1 N hydrochloric acid at ice bath temperature. To the resulting slurry was added a solution of sodium nitrite (21.6 g, 313 mmole) in 90 ml of water. The resulting brown solution was stirred at ice bath temperature for 45 minutes and treated dropwise with a solution of tin (II) chloride dihydrate (82.0 g, 363.0 mmole) in 90 ml of concentrated hydrochloric acid. The reaction was stirred for 1 hour at 5° C. and the hydrazine hydrochloride salt was collected by filtration. This was then dissolved in 300 ml of 3N sodium hydroxide solution and the aqueous solution was extracted with diethyl ether (2×200 ml). The combined organic layers were dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to give 18.5 g (84% crude yield) of the titled hydrazine as brown solid which melts around room temperature.

Provenance & Evidence