Reacción #975433

Ecuación de reacción

2-amino-5-bromo-N,3-dimethylbenzamide

1-methylnaphthalene

sodium cyanide

→

title compound

2-amino-5-cyano-N,3-dimethylbenzamide

Disolventes

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA 100-mL, three-necked flask equipped with a mechanical stirrer
2. 2
   Temperaturawhile maintaining a flow of nitrogen through a gas inlet line
3. 3
   TemperaturaThe mixture was heated at 160 to 165° C. for 4.25 h
4. 4
   Temperaturato cool to 25° C
5. 5
   workup.STIRRINGwhile stirring
6. 6
   workup.STIRRINGAfter stirring for an additional 30 minutes
7. 7
   Filtraciónthe reaction mixture was filtered
8. 8
   Otrothe solid collected
9. 9
   Lavadowas washed with water (3×10 mL) and xylenes (10 mL)
10. 10
    Otrodried to a constant weight in a vacuum-oven at 50° C.

Procedimiento

A 100-mL, three-necked flask equipped with a mechanical stirrer, thermometer and condenser was charged with 2-amino-5-bromo-N,3-dimethylbenzamide (prepared by the method of Reference Example 1) (5.0 g, 0.020 mol, 99.1% purity) and 1-methylnaphthalene (20 g) while maintaining a flow of nitrogen through a gas inlet line connected to the condenser. The reaction mixture was stirred at room temperature, and powdered sodium cyanide (powdered just prior to use) (1.25 g, 0.024 mol, assuming 95% purity), copper(I) iodide (0.57 g, 0.0030 mol) and 4-(dimethylamino)pyridine (2.10 g, 0.017 mol) were added. The mixture was heated at 160 to 165° C. for 4.25 h and then allowed to cool to 25° C. Water (20 mL) was added dropwise to the reaction mixture over 5 minutes while stirring. After stirring for an additional 30 minutes, the reaction mixture was filtered, and the solid collected was washed with water (3×10 mL) and xylenes (10 mL), and then dried to a constant weight in a vacuum-oven at 50° C. to give the title compound as a light brown solid (3.9 g).

Fuente