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 (1.47 g, 7.7 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 3,5-lutidine (1.98 g, 18.5 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 allowed to cool to room temperature overnight. The solid reaction mixture was heated at 155° C. for 2 h, and then more anisole (15 mL) and powdered sodium cyanide (0.779 g, 15.4 mmol) were added to the mixture. The reaction mixture was taken out of the glovebox, heated at about 115° C. and water (45 mL) was added over 5 minutes. After cooling to room temperature, the reaction mixture was filtered. The solid collected was washed with water (2×15 mL) and toluene (2×15 mL), and then dried in a vacuum-oven at 40° C. to give the title compound as an off-white solid (5.53 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 heated at 155° C. for 2 h
5. temperatureheated at about 115° C.
6. temperatureAfter cooling to room temperature
7. filtrationthe reaction mixture was filtered
8. customThe solid collected
9. washwas washed with water (2×15 mL) and toluene (2×15 mL)
10. customdried in a vacuum-oven at 40° C.

ORD record

ord-50acad122ee1475ebd93006afcedeed6

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247570B2