Oxygen → 2-Amino-5-cyano-N,3-dimethylbenzamide

Temperature

155 °C

A 100-mL, four-necked flask equipped with a magnetic stirrer, thermocouple and condenser was charged with copper(I) iodide (0.88 g, 4.6 mmol), powdered sodium cyanide (1.87 g, 37.0 mmol, 97% purity), 2-amino-5-bromo-N,3-dimethylbenzamide (prepared by the method of Reference Example 1) (7.50 g, 30.9 mmol), oxygen-free 4-methoxypyridine (0.505 g, 4.6 mmol) and oxygen-free anisole (15 mL) under a nitrogen atmosphere in a glovebox. The reaction mixture was heated at about 155° C. for 12 h and then allowed to cool to room temperature overnight. The solid reaction mixture was then heated at 155° C., and then more copper iodide (0.588 g. 4.6 mmol) was added. After about 3 h, more anisole (15 mL) and powdered sodium cyanide (0.779 g, 15.4 mmol) were added to the reaction mixture, the mixture was cooled to 110° C., and then water (30 mL) was added. The reaction mixture was taken out of the glovebox, allowed to cool to room temperature and filtered. The solid collected was washed with water (3×15 mL) and toluene (2×15 mL), and then dried in a vacuum-oven at 55° C. to give the title compound as an off-white solid (5.22 g).

1. customA 100-mL, four-necked flask equipped with a magnetic stirrer
2. temperatureto cool to room temperature overnight
3. customThe solid reaction mixture
4. temperaturewas then heated at 155° C.
5. temperaturethe mixture was cooled to 110° C.
6. temperatureto cool to room temperature
7. filtrationfiltered
8. customThe solid collected
9. washwas washed with water (3×15 mL) and toluene (2×15 mL)
10. customdried in a vacuum-oven at 55° C.

ORD record

ord-5d7980914c58401da96d4cbdd9364e67

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247570B2