Pyridine → Diethyl (4-chloroanilino)propanedioate

HRID 905116Notes

Reaction equation

HRID 905116 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br[CH:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].N1C=CC=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 78124-ChloroanilineHCID 69637Diethyl bromomalonate

Product 1

HCID 246045Diethyl (4-chloroanilino)propanedioateYield 35%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  1. temperatureThe mixture was refluxed
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionwater was added
  4. extractionThe mixture was extracted with chloroform twice
  5. washThe chloroform layers were washed with water twice
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue (3.34 g) was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d5a14dfe5d9646cfa9893f554dc8ec6a
Source dataset
uspto-grants-1983_12
Patent number
US04421914

Reaction notes

Loading…