Acetone → 7-methoxy-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 383906Notes

Reaction equation

HRID 383906 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.C1([C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)O)O.[CH3:18]C(C)=O>II>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([C:14]([CH3:12])=[CH:15][C:16]([CH3:17])([CH3:18])[NH:9]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 289CatecholHCID 108243-Methoxyaniline

Product 1

HCID 6434787-methoxy-2,2,4-trimethyl-1,2-dihydroquinolineYield 35%

Reagents, catalysts & solvents 1

HCID 807IodineCatalyst

Procedure

To a solution of m-anisidine (400 g) in acetone (7.21) were added catechol (33 g) and iodine (27 g), and the mixture was heated under reflux for 4 days. The reaction mixture filtered through silica gel and the solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=10:1→5:1) to give the title compound (234 g, 35%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 days
  3. filtrationThe reaction mixture filtered through silica gel
  4. customthe solvent was evaporated under reduced pressure
  5. washThe residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=10:1→5:1)

Sources & evidence

ORD record
ord-70688bf2905e463f92c4505f3201574d
Source dataset
uspto-grants-2013_02
Patent number
US08367695B2

Reaction notes

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