Iodine → 6-(2-Methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 25748Notes

Reaction equation

HRID 25748 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1.II.S([O-])([O-])(=O)=O.[Mg+2]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:12](=[CH:13][CH:14]=1)[NH:15][C:4]([CH3:9])([CH3:5])[CH:3]=[C:8]2[CH3:7]

Participants

5

Reactant 3

HCID 807IodineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 27595594-(2-Methoxyphenyl)aniline

Product 1

HCID 225665156-(2-Methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinolineYield 34.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 10 g of 2-methoxy-4′-aminobiphenyl, 4.4 g of iodine, 44 g of magnesium sulfate and 600 mL of acetone was heated in a sealed flask at 120° C. overnight. The reaction mixture was cooled down to room temperature and filtered through diatomaceous earth. The residue was rinsed with acetone and the solvent was evaporated in vacuo. The residue was purified by flash chromatography to yield 2.4 g of 6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline as a foam.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. washThe residue was rinsed with acetone
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-512ca0c41eec426e88eb577eaf8be62c
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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