O-Toluidine → HCID 835259, compound

To a 500 mL 3-neck round bottom flask was added o-toluidine (3.60 g, 33.6 mmol) and 150 mL toluene. The solution was cooled in an ice bath under nitrogen. Trimethylaluminum (2.0 M in toluene, 23.51 ml, 47.0 mmol) was added dropwise via dropping funnel. The reaction mixture was stirred at room temperature for 2 hours. Next, 3-iodobenzonitrile (10 g, 43.7 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 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. The solid was triturated with hexane, filtered, washed with hexane (7.77 g, 69%).

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
8. customThe solid was triturated with hexane
9. filtrationfiltered
10. washwashed with hexane (7.77 g, 69%)

ORD record

ord-777ea94e8b9b4091b274be29389e6c6c

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871361B2