Dimethyl Sulfoxide → 4-[(2-hydroxyethyl)amino]benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-fluorobenzonitrile (6.06 g), 2-aminoethanol (3.71 g), potassium carbonate (8.29 g) and dimethylsulfoxide (50 mL) was stirred at 100° C. overnight. To the reaction solution was added water (200 mL), and extracted with ethyl acetate (200 mL×4). The ethyl acetate layer was washed with saturated brine (100 mL), and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (eluted with ethyl acetate:hexane=30:70, then 50:50, then 80:20, then ethyl acetate) to give 4-[(2-hydroxyethyl)amino]benzonitrile as yellow solid (5.89 g).

Provenance & Evidence