2-Chloroaniline → HCID 131710395, compound

HRID 918140Notes

Reaction equation

HRID 918140 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:14]1[C:12](=[O:13])[CH2:11][C:10]([CH3:18])([CH3:9])[CH2:17][CH:15]=1

Participants

5

Reactant 2

HCID 72402-ChloroanilineHCID 31358Dimedone

Product 1

HCID 131710395HCID 131710395, 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 ispropyl 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. Elementary analysis: C14H16NOCL Calcd. C, 67.32; H, 6.45; N, 5.60 Found C, 67.13; H, 6.31; N, 5.82 (b) A mixture of 40 parts of dimedone and 36.4 parts of 2-chloroaniline is heated at 170°-175°C for 45 minutes followed by cooling. The resulting reaction product is recrystallized to obtain yellow cubes. The crystals are collected by filtration, washed well with isopropyl ether and recrystallized from acetone. The procedure yields colorless prisms of 3-(2-chloroanilino)-5,5-dimethyl-2-cyclohexen-1-one. Melting point: 150°-152°C. By procedures similar to those described in Example 1-(a) and (b), the following compounds are produced.

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 ispropyl ether
  8. customrecrystallized from acetone

Sources & evidence

ORD record
ord-7731fcbc3aa8456a9865bb6a9191f99b
Source dataset
uspto-grants-1976_07
Patent number
US03969409

Reaction notes

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