1-Methylnaphthalene → 2-Amino-5-cyano-N,3-dimethylbenzamide

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-picoline (1.60 g, 0.017 mol) were added. The mixture was heated at 158 to 162° C. for 6 h, and then transferred to a 200-mL flask and allowed to cool overnight. Water (20 mL) was added dropwise to the reaction mixture over 5 minutes while stirring. After stirring for an additional 2 h, 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 (2.8 g).

1. customA 100-mL, three-necked flask equipped with a mechanical stirrer
2. temperaturewhile maintaining a flow of nitrogen through a gas inlet line
3. temperatureThe mixture was heated at 158 to 162° C. for 6 h
4. customtransferred to a 200-mL flask
5. temperatureto cool overnight
6. stirringwhile stirring
7. stirringAfter stirring for an additional 2 h
8. filtrationthe reaction mixture was filtered
9. customthe solid collected
10. washwas washed with water (3×10 mL) and xylenes (10 mL)
11. customdried to a constant weight in a vacuum-oven at 50° C.

ORD record

ord-781ca12fc97244c2a017c74c64043996

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247570B2