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

HRID 1502629Notes

Reaction equation

HRID 1502629 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-6041df373048492d9971a9441397e224
Source dataset
uspto-grants-2015_12
Patent number
US09211287B2

Reaction notes

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