Ethyl Acetate → 3-(4-Chloro-2-iodophenylamino)cyclohex-2-enone

HRID 715204Notes

Reaction equation

HRID 715204 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([I:9])[CH:3]=1.[C:10]1(=O)[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH2:11]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH:11]=2)=[C:4]([I:9])[CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 104341,3-CyclohexanedioneHCID 521998p-Toluenesulfonic acid monohydrateHCID 27576154-Chloro-2-iodoaniline

Product 1

HCID 673287853-(4-Chloro-2-iodophenylamino)cyclohex-2-enoneYield 80.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-2-iodoaniline (0.5 g, 1.97 mmol), 1,3-cyclohexanedione (0.22 g, 1.96 mmol) and p-toluenesulfonic acid monohydrate (catalytic) in toluene (6 mL) were heated to reflux for 2 h. The reaction was cooled and EtOAc (50 mL) was added and the organic phase was washed with water (20 mL) and brine (20 mL), dried over sodium sulfate, filtered and evaporated to give a brown solid, which was purified by column chromatography [Silica, eluent: EtOAc:hexane to give 3-(4-chloro-2-iodophenylamino)cyclohex-2-enone as a yellow solid (0.55 g, 80%).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 2 h
  3. temperatureThe reaction was cooled
  4. washthe organic phase was washed with water (20 mL) and brine (20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a brown solid, which
  9. customwas purified by column chromatography [Silica, eluent

Sources & evidence

ORD record
ord-b1b1be39df864d7ba0a1c0582eb69990
Source dataset
uspto-grants-2015_11
Patent number
US09187471B2

Reaction notes

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