2-Chloroaniline → HCID 13002203, compound

HRID 461670Notes

Reaction equation

HRID 461670 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][C:10]1([CH3:18])[CH2:17][C:15](=O)[CH2:14][C:12](=[O:13])[CH2:11]1>C(O)C.C(O)(=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:15]1[CH2:17][C:10]([CH3:18])([CH3:9])[CH2:11][C:12](=[O:13])[CH:14]=1

Participants

5

Reactant 2

HCID 72402-ChloroanilineHCID 31358Dimedone

Product 1

HCID 13002203HCID 13002203, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of 12.75 parts of 2-chloroaniline and 14 parts of dimedone is dissolved in 40 volume parts of ethanol under warming, followed by the addition of 3 drops of glacial acetic acid. The solution is refluxed in a water bath for 2 hours, after which time the ethanol is distilled off and the resulting residue is allowed to cool, whereupon yellow crystals separate. These crystals are collected by filtration, washed with isopropyl ether and recrystallized from acetone. The procedure yields 3-(2-chloroanilino)-5,5-dimethyl-2-cyclohexen-1-one as colorless prisms melting at 150°-152° C.

Workup

  1. temperatureunder warming
  2. temperatureThe solution is refluxed in a water bath for 2 hours
  3. distillationafter which time the ethanol is distilled off
  4. temperatureto cool
  5. customwhereupon yellow crystals separate
  6. filtrationThese crystals are collected by filtration
  7. washwashed with isopropyl ether
  8. customrecrystallized from acetone

Sources & evidence

ORD record
ord-6c8f98a6b9d14018a65478f83f65df90
Source dataset
uspto-grants-1977_12
Patent number
US04064133

Reaction notes

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