O-Toluidine → 3-methoxy-N-(2-methylphenyl)benzamide

To a 500 mL 3-neck round bottom flask was added o-toluidine (4.50 g, 42.0 mmol) and 150 mL toluene. The solution was cooled in an ice bath under nitrogen. Trimethylaluminum (2.0 M in toluene, 29.4 ml, 58.8 mmol) was added dropwise via dropping funnel. The reaction mixture was stirred at room temperature for 2 hours under nitrogen. Next, 3-methoxybenzonitrile (7.27 g, 54.6 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 and washed with dichloromethane and methanol. The filtrate was evaporated leaving a solid. The solid was triturated with hexane, filtered, washed with hexane (6 g, 59%).

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
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 (6 g, 59%)

ORD record

ord-bd13f8143c4043b6aa429cbda7b4e24a

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871361B2