Aluminum(III) Chloride → HCID 58174254, compound

Participants

Reaction Steps

To a solution of AlCl3 (268 mg, 1.8 mmol) in Et2O cooled to 0° C. in an ice bath was added LiAlH4 (66 mg, 1.8 mmol) in one portion, under N2. After stirring 15 min, a solution of [6-(4-trifluoromethylphenoxy)-pyridin-3-yl]-acetonitrile (500 mg, 1.8 mmol) in Et2O (2 mL) and THF (1 mL) was added dropwise resulting in an exotherm. The reaction was allowed to cool to room temperature, and after 2 h, the reaction was quenched by careful addition of 5 mL of saturated aqueous ammonium chloride. The resulting mixture was made alkaline by addition of 2M NaOH solution. The precipitate which formed was removed by filtration through Celite. The filtrate phases were separated, and the aqueous phase was extracted 3 times with Et2O. The pooled organic fractions were dried with Na2SO4 and suction filtered. The solvent was removed in vacuo to yield 2-[6-(4-trifluoromethylphenoxy)-pyridin-3-yl]-ethylamine (200 mg), as a brown oil.

Provenance & Evidence