Methanol → 2-[4-(Trifluoromethyl)phenyl]ethan-1-amine

Participants

Reaction Steps

Lithium aluminum hydride (0.558 g, 14. 7 mmol) was suspended in THF (10 ml), to which a solution of 1-(2-nitrovinyl)-4-trifluoromethylbenzene (1.596 g, 7.35 mmol) prepared in Reference Example 118 in THF (10 ml) was added dropwise while cooling in an ice-bath, and the mixture was heated under reflux for 2 hours. Methanol was slowly added to the mixture until it no longer foamed. Water (0.6 ml), 15% sodium hydroxide aqueous solution (0.6 ml) and water (1.8 ml) were added in this order, and the insoluble substances were removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel with an amine-treated surface (Fuji Silysia; NH-DM1020, solvent; methylene chloride/n-hexane=4/1) to afford 2-(4-trifluoromethylphenyl)ethylamine (0.431 g, yield 31%) as an orange-colored oil.

Provenance & Evidence