Water → 2-[4-(Aminomethyl)phenyl]benzonitrile

Participants

Reaction Steps

A solution of 4-azidomethyl-2'-cyanobiphenyl (4.68 g, 20 mmole) in 40 ml of dry tetrahydrofuran (THF) was stirred under N2 at room temperature as 5.3 g (20 mmole) of triphenylphosphine was added in small portions over a period of about 10 minutes. After 2 hours, by which time gas evolution had ceased, 532 μl (532 mg, 29.6 mmole) of H2O was added. After an additional 23 hours, the solution was concentrated in vacuo to give a pale golden gum. This material was chromatographed on a column of silica gel (50×8.5 cm) packed in CH2Cl2. The column was eluted with a gradient of 0-6% methanol in CH2Cl2. Concentration of the product fractions gave a foam which solidified upon trituration with ether. This material was collected on a filter, washed further with some ether, and dried in vacuo at 50° C. to give white crystals, of satisfactory purity; mass spectrum (FAB) m/e 209 (M+1)+.

Provenance & Evidence