Reaction #2517

Reaction equation

sodium bicarbonate

o-anisidine

4-nitrobenzoic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

title compound

Yield 87.5%

4-Nitro-N-(2-methoxyphenyl)benzamide

Yield 87.5%

Solvents

methylene chloride

Conditions

Workup

1. 1
   TemperatureWith cooling in an ice bath
2. 2
   Extractionextracted with methylene chloride
3. 3
   Washwashed with water and saturated brine in that order
4. 4
   DryingAfter drying on anhydrous magnesium sulfate
5. 5
   Otherthe solvent was removed by evaporation
6. 6
   Otherthe resulting solid material was purified by silica gel column chromatography (methylene chloride)

Procedure

With cooling in an ice bath, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (630 mg, 3.29 mmol) was added to 15 ml of methylene chloride solution containing o-anisidine (368 mg, 2.99 mmol) and 4-nitrobenzoic acid (500 mg, 2.99 mmol). After 1 hour of stirring at the same temperature, the reaction mixture was roughly adjusted to pH 8 with saturated sodium bicarbonate aqueous solution, extracted with methylene chloride and then washed with water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting solid material was purified by silica gel column chromatography (methylene chloride) to obtain 712 mg (87.4%) of the title compound in the form of yellow powder.

Source