2-Chloroaniline → HCID 20477365, compound

HRID 905117Notes

Reaction equation

HRID 905117 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].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:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][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 72402-ChloroanilineHCID 69637Diethyl bromomalonate

Product 1

HCID 20477365HCID 20477365, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

o-Chloroaniline (15.9 g) was dissolved in dry toluene (20 ml), and diethyl bromomalonate (12.0 g) was added. The mixture was heated under reflux with stirring for 10 hours. The reaction mixture was washed with dilute hydrochloric acid, then with water three times, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using benzene as an eluent to give 5.1 g (yield 36%) of diethyl o-chloroanilinomalonate which had the following NMR data.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. washThe reaction mixture was washed with dilute hydrochloric acid
  4. dry with materialwith water three times, and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8a7a284132cd46fd8955df4b2ceae5a0
Source dataset
uspto-grants-1983_12
Patent number
US04421914

Reaction notes

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