Diisopropylaniline → HCID 178490167, compound

Participants

Reaction Steps

To a 500 mL 3-neck round bottom flask was added 2,6-diisopropylaniline (4.82 g, 27.2 mmol) and 100 mL toluene. The solution was cooled in an ice bath under nitrogen and trimethylaluminum (2.0 M in toluene, 19 mL, 38.1 mmol) was added dropwise via dropping funnel. The reaction mixture was stirred at room temperature for 2 hours. Next, 3-methoxy-5-methylbenzonitrile (5.20 g, 35.3 mmol) in 50 mL toluene was added and the reaction mixture was heated to 70° C. overnight under nitrogen. The reaction mixture was cooled in an ice bath and was poured onto a stirring slurry of silica gel in 2:1 dichloromethane/methanol (v/v). The silica gel was filtered off and washed with dichloromethane and methanol. The filtrate was evaporated leaving a solid. Hexane was added to the solvent and the solid was filtered off and washed with hexane (5.83 g, 66%).

Provenance & Evidence