Diethyl Ether → 4-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]aniline

Participants

Reaction Conditions

Reaction Steps

2-(6-Methyl-pyridin-3-yl)-N-p-tolyl-acetamide (0.960 g, 4 mmol) was dissolved in dry THF (20 cm3), and cooled to 0° C. LiAlH4 (5.0 eq., 20 mmol, 10 ml of a 2.0 M solution in THF) was added dropwise at first, until no more gas evolution was observed (˜0.5 ml), and then the remaining LiAlH4 solution was added in one portion. The resulting solution was heated to reflux for 16 hours with stirring. Wet diethyl ether was then added until no further gas evolution was observed, the resulting medium filtered, and the residue washed with ether (˜50 cm3). The filtrate was dried (MgSO4), and the solvent removed to yield a crude yellow oil. The oil was purified by flash chromatography, eluting with 1:1 petrol (40-60)/EtOAc. The product was collected as the fraction with Rf=0.294. The product was obtained as a pale yellow oil (254 mg, 28%).

Provenance & Evidence