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 (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).

Provenance & Evidence