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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence