4-Chloroaniline → HCID 15086648, compound

HRID 359105Notes

Reaction equation

HRID 359105 reaction equation
[CH2:1]([CH:3]([C:9]([O:11]CC)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C(OCC)(=O)C>[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:9]([CH:3]([CH2:1][CH3:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:11])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 8610Diethyl ethylmalonate

Product 1

HCID 15086648HCID 15086648, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

Diethyl 2-ethylmalonate (8.76 ml) and p-chloroaniline (4 g) were dissolved by heating at 130° C. for 11 hours, and the mixture was cooled and dissolved in ethyl acetate, and further, the mixture was washed successively with 1N hydrochloric acid, aqueous sodium bicarbonate solution, and water, and concentrated under reduced pressure. The resulting residue was subjected to column chromatography on silica gel and eluted with chloroform to give the oily desired product (6.66 g).

Workup

  1. temperaturethe mixture was cooled
  2. washfurther, the mixture was washed successively with 1N hydrochloric acid, aqueous sodium bicarbonate solution, and water
  3. concentrationconcentrated under reduced pressure
  4. washeluted with chloroform

Sources & evidence

ORD record
ord-74b4bcc07ef34a868f69532ad9f05354
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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