diethyl 2-(3-chloroanilino)propanedioate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: m-Chloroaniline (12.8 g) and diethyl bromomalonate (9.6 g) were dissolved in dry toluene (20 ml). The solution was heated under reflux with stirring for 3 hours. The reaction mixture was washed with dilute hydrochloric acid and then three times with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was washed with n-hexane to give 3.3 g (yield 29%) of diethyl m-chloroanilinomalonate having the following NMR data. The solution was heated under reflux The reaction mixture was washed with dilute hydrochloric acid three times with water, and dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure The residue was washed with n-hexane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: m-Chloroaniline (12.8 g) and diethyl bromomalonate (9.6 g) were dissolved in dry toluene (20 ml). The solution was heated under reflux with stirring for 3 hours. The reaction mixture was washed with dilute hydrochloric acid and then three times with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was washed with n-hexane to give 3.3 g (yield 29%) of diethyl m-chloroanilinomalonate having the following NMR data. The solution was heated under reflux The reaction mixture was washed with dilute hydrochloric acid three times with water, and dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure The residue was washed with n-hexane