Benzonitrile, 4-(1-aminoethyl)- synthesis

Yield: 91%

Reaction Conditions:

with Cp*IrCl(N-(phenyl(pyridin-2-yl)methyl)methanesulfonamide)complex;ammonium formate;acetic acid in methanol at 60; for 4 h;Inert atmosphere;

Steps:

13 Reaction Example 13 Synthesis of 4-(1-aminoethyl)benzonitrile
In a 20-mL Schlenk, catalyst 3 (MW: 624.22) (6.24 mg, 0.010 mmol, S/C=500) was charged, then dried under reduced pressure and replaced with argon gas. Methanol (5 mL), 4-acetyl benzonitrile (MW: 145.16) (726 mg, 5.0 mmol), ammonium formate (MW: 63.06) (946 mg, 15 mmol), and acetic acid (MW: 60.05) (286 μL, 5.0 mmol) were added thereto, and the mixture was stirred with heating at 60° C. for 4 h. The solvent was concentrated under reduced pressure, 1 M KOH (25 mL) was added, and the mixture was extracted with dichloromethane (40 mL), then the organic layer was dried over sodium sulfate, filtered, and diluted in a 50-mL measuring flask. Five mL of the solution was taken, the solvent was distilled off, and quantification by H-NMR was carried out using coumarin as the internal standard substance (91% yield).

References:

Kanto Kagaku Kabushiki Kaisha;Watanabe, Masahito;Takemoto, Toshihide;Tanaka, Kouichi;Murata, Kunihiko US2016/60282, 2016, A1 Location in patent:Paragraph 0200