1,3-Dimethyl-2-imidazolidinone → 4-Methoxy-2-methylquinolin-8-ol

HRID 864576Notes

Reaction equation

HRID 864576 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.CN1CCN(C)[C:16]1=[O:21].C[O-].[Na+]>CO>[OH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:13])[CH:3]=[C:2]2[O:21][CH3:16]

Participants

5

Reactant 3

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 10942334Sodium MethoxideHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 183218914-Methoxy-2-methylquinolin-8-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-8-hydroxy-2-methylquinoline (9 g), 1,3-dimethyl-2-imidazolidinone (100 ml) and 28% solution of sodium methoxide in methanol (135 ml) was stirred at 150° C. for 4 hours. The reaction mixture was cooled to ambient temperature followed by partition into ethyl acetate and water. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The crystalline residue was washed with n-hexane to give 8-hydroxy-4-methoxy-2-methylquinoline (5.57 g).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customby partition into ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. washThe crystalline residue was washed with n-hexane

Sources & evidence

ORD record
ord-6cc47415f3164f418fca43b418f003ae
Source dataset
uspto-grants-1996_10
Patent number
US05563162

Reaction notes

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