4-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]-N-nitrosoaniline → 1-(4-Methylphenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine

Participants

Reaction Steps

Crude 2-methyl-5-(N-nitroso-2-p-tolylaminoethyl)pyridine (612 mg, 2.4 mmol) was dissolved in dry THF (20 cm3) in a dry 3-neck flask under an argon atmosphere and cooled until the internal temperature was between 0-5° C. Solid LiAlH4 (290 mg, 7.7 mmol) was added and the reaction allowed to warm to room temperature. Following 2 hours stirring at room temperature, the reaction was again cooled to 0° C., and quenched with MeOH until no further gas evolution was observed (˜3 cm3). Saturated NaOH solution was then added (3 cm3), followed by H2O (3 cm3), and the medium extracted with CHCl3 (3×50 cm3), the combined extracts were dried (MgSO4), and solvent removed in vacuo to yield a crude orange oil. This could be carried forward to the next step if desired, or stored below 5° C. until required.

Provenance & Evidence