Pyridine → Diethyl (4-chloroanilino)propanedioate

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Reaction Steps

p-Chloroaniline (2 g) was dissolved in dry benzene (20 ml), and diethyl bromomalonate (3.8 g) and then dry pyridine (1.3 ml) were added. The mixture was refluxed with stirring overnight. The solvent was distilled off under reduced pressure, and then water was added. The mixture was extracted with chloroform twice. The chloroform layers were washed with water twice and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue (3.34 g) was purified by silica gel column chromatography using benzene as an eluent to give 1.56 g (yield 35%) of diethyl p-chloroanilinomalonate having the following NMR data.

Provenance & Evidence