Hydrochloric Acid → Nonan-3-ylhydrazine

Participants

Reaction Steps

34.84 g (135.9 mmol) of tert-butyl N′-(1-ethyl-heptylidene)-hydrazinecarboxylate are dissolved in a mixture of 100 ml of THF and 150 ml of methanol and, after 9.93 g (157.6 mmol) of sodium cyanoborohydride have been added, the mixture is stirred for 2 hours at room temperature. 97 ml of 6N HCl are added dropwise and, after the addition has ended, the mixture is refluxed for 1.5 hours. It is neutralized with 6N NaOH solution, then, after the non-aqueous solvents have been removed, extracted three times with dichloromethane, and, after the mixture has been dried over sodium sulphate, the solvent is removed in vacuo. This gives 19.78 g (92%) of a yellow oil.

Provenance & Evidence