2-Nitrophenol → HCID 18757072, compound

Participants

Reaction Conditions

Reaction Steps

2-nitrophenol (0.56 g, 0.004 mole) is added in portions to a stirred suspension of sodium hydride (160 mg of a dispersion at 60% in oil, 0.004 mole) in dry dimethylformamide (10 ml) in a nitrogen atmosphere. When the hydrogen evolution is completed, while stirring, a solution of N-[4-{benzyl (2-chloroethyl)amino}butyl]benzamide (1.6 g, 0.0046 mole) in dry dimethylformamide (5 ml) is added dropwise. The reaction mixture is heated to 65-70 degrees C. for 1.5 hours, cooled back to ambient temperature, and poured over crushed ice. The mixture is extracted with ether (50 ml); the organic phase is separated and washed with water (3×20 ml) before being dried over magnesium sulfate. Filtration and evaporation of the solvent at reduced pressure yield 1.3 g of an oil which is purified by flash chromatography over silica gel by using a mixture of ethyl acetate/heptane (3/1) as eluant. The expected compound is obtained in the form of oil (0.94 g, 52%).

Provenance & Evidence