Aniline → HCID 178490388, compound

To a 500 mL 3-neck round bottom flask was added aniline (5.38 g, 57.8 mmol) and 150 mL toluene. The solution was cooled in an ice bath under nitrogen. Next trimethylaluminum solution in toluene was added dropwise via dropping funnel (2.0 M, 40.4 mL, 81 mmol) and the reaction mixture was stirred at room temperature for 2 h. Next 3-methoxybenzonitrile (10 g, 75 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 then poured onto a stirring slurry of silica gel in 2:1 dichloromethane/methanol. The silica gel was filtered off and washed with dichloromethane and methanol. The filtrate was evaporated leaving a solid which was triturated with hexane, filtered, and washed with more hexane and dried to give desired product (7.81 g, 60%).

1. temperatureThe solution was cooled in an ice bath under nitrogen
2. temperaturethe reaction mixture was heated to 70° C. overnight under nitrogen
3. temperatureThe reaction mixture was cooled in an ice bath
4. filtrationThe silica gel was filtered off
5. washwashed with dichloromethane and methanol
6. customThe filtrate was evaporated
7. customleaving a solid which
8. customwas triturated with hexane
9. filtrationfiltered
10. washwashed with more hexane
11. customdried

ORD record

ord-ebef1a96f5534827b8f0dbaee331fc2e

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871361B2