Synthesis
The general procedure for the synthesis of (2-(aminomethyl)phenyl)boronic acid from 2-cyanophenylboronic acid was as follows: to a methanol solution (20 mL) containing 2-cyanophenylboronic acid (300 mg, 2.0 mmol) was added nickel ryenne (100 mg, 10% w/w). The reaction mixture was stirred for 4 h at room temperature under hydrogen pressure of 50 psi. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad and the filtrate was concentrated under vacuum to afford (2-(aminomethyl)phenyl)boronic acid 150 mg (48.7% yield) as a white solid. Mass spectrum (electrospray positive ion mode): m/z = 152.20, 153.40, 154.35, 155.65 [M + H]+. Analyzed by liquid chromatography-mass spectrometry: retention time tR = 0.76 min.
