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

HRID 1604519Notes

Reaction equation

HRID 1604519 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

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°0 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. customby partition into ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. washThe crystalline residue was washed with n-hexane

Sources & evidence

ORD record
ord-f5c3e807fe29435a96e3345ef1e3b460
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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