Aniline → Diethyl anilinopropanedioate

HRID 905119Notes

Reaction equation

HRID 905119 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C1C=CC=CC=1>[NH:1]([CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 69637Diethyl bromomalonate

Product 1

HCID 299984Diethyl anilinopropanedioateYield 30%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Aniline (18.6 g) was dissolved in dry benzene (125 ml), and diethyl bromomalonate (23.9 g) was added. The mixture was heated under reflux for 37 hours with stirring. The reaction mixture was washed with dilute hydrochloric acid to remove the unreacted aniline. The benzene layer was washed with water three times, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using hexane/ethyl acetate (10:1) as an eluent to give 7.5 g (yield 30%) of diethyl anilinomalonate having the following NMR data.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 37 hours
  3. washThe reaction mixture was washed with dilute hydrochloric acid
  4. customto remove the unreacted aniline
  5. washThe benzene layer was washed with water three times
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ca97de63779e4fb19d62fd430ead197f
Source dataset
uspto-grants-1983_12
Patent number
US04421914

Reaction notes

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