3-Chloroaniline → diethyl 2-(3-chloroanilino)malonate

HRID 905118Notes

Reaction equation

HRID 905118 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Br[CH:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH:5][CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 69637Diethyl bromomalonate

Product 1

HCID 246044diethyl 2-(3-chloroanilino)malonateYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux
  3. washThe reaction mixture was washed with dilute hydrochloric acid
  4. dry with materialthree times with water, and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washThe residue was washed with n-hexane

Sources & evidence

ORD record
ord-e950db0cd81e4c9397ecf5da403a043b
Source dataset
uspto-grants-1983_12
Patent number
US04421914

Reaction notes

Loading…