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

Temperature

153 °C

A 100-mL, four-necked flask equipped with a magnetic stirrer, thermocouple and condenser was charged with copper(I) iodide (1.01 g, 5.3 mmol), 2-amino-5-bromo-N,3-dimethylbenzamide (prepared by the method of Reference Example 1) (5.00 g, 20.6 mmol), powdered sodium cyanide (1.27 g, 25.1 mmol, 97% purity), oxygen-free 4-picoline (1.92 g, 20.6 mmol) and oxygen-free anisole (10 mL) under a nitrogen atmosphere in a glovebox. The reaction mixture was heated at about 153° C. for 12 h and allowed to cool to room temperature overnight. The solid reaction mixture was then heated at 125° C. and more anisole (10 mL) was added. A solution of sodium cyanide (0.505 g, 10.0 mmol) in water (20 mL) was added to the reaction mixture at about 105° C., and then the mixture was taken out of the glovebox and allowed to cool to room temperature while stirring. The reaction mixture was filtered, and the solid collected was washed with water (2×10 mL, 1×5 mL) and toluene (2×10 mL), and then dried in a vacuum-oven at 55° C. to give the title compound as an off-white solid (3.66 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 125° C.
5. temperatureto cool to room temperature
6. filtrationThe reaction mixture was filtered
7. customthe solid collected
8. washwas washed with water (2×10 mL, 1×5 mL) and toluene (2×10 mL)
9. customdried in a vacuum-oven at 55° C.

ORD record

ord-f911b57cdbd041f6b5e08a1a6692a85b

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247570B2