2-Methoxyaniline → 4-cyano-N-(2-methoxyphenyl)benzamide

In an atmosphere of dry air, 4-cyanobenzoic acid (1.5 g, 10 mmol) was dissolved in benzene (5 ml), and DMF (0.1 ml) and thionyl chloride (2.2 ml, 30 mmol) were added dropwise to the resulting solution at room temperature, followed by 30 minutes of heating under reflux. After removing the solvent by evaporation, the resulting residue was subjected to azeotropy using benzene (10 ml×2) to obtain a yellow solid which was subsequently dissolved in methylene chloride (10 ml) and mixed with o-anisidine (1.16 ml, 10 mmol) and 20% sodium hydroxide aqueous solution (4 ml) with cooling in an ice bath. After 20 minutes of stirring at the same temperature, the resulting mixture was extracted with methylene chloride and then washed with 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting light yellow solid was purified by recrystallization (methylene chloride-ether) to obtain 2.36 g (93.6%) of the title compound in the form of creamy-colored crystals.

1. temperatureof heating
2. temperatureunder reflux
3. customAfter removing the solvent
4. customby evaporation
5. customto obtain a yellow solid which
6. temperaturewith cooling in an ice bath
7. extractionthe resulting mixture was extracted with methylene chloride
8. washwashed with 1N hydrochloric acid, water and saturated brine in that order
9. dry with materialAfter drying on anhydrous magnesium sulfate
10. customthe solvent was removed by evaporation
11. customthe resulting light yellow solid was purified by recrystallization (methylene chloride-ether)

ORD record

ord-942a079fe8694bdda867bffdec3990b6

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05728835