4-amino-3,5-dimethylbenzonitrile → 4-(Aminomethyl)-2,6-dimethylaniline

Participants

Reaction Steps

Step AN2. To the suspension of 0.26 g of lithium aluminum hydride in 30 mL of THF was added dropwise a solution of 0.49 g of 4-amino-3,5-dimethylbenzonitrile in 5 mL of THF. The reaction mixture was stirred at reflux for 3 hours and cooled to room temperature. The reaction mixture was quenched with 1.0 mL of 1.0 N NaOH aqueous solution. The precipitate was filtered off and the solvent was evaporated in vacuo to provide the crude product, which can be used without purification. A portion of the crude product was purified by preparative HPLC. LCMS (method B) RT 0.152 min., (2M+H)+ 301. 1H NMR (500 MHz, CD3OD) δ 7.04 (s, 2 H), 3.95 (s, 2 H), 2.25 (s, 6 H).

Provenance & Evidence