Methanol → 2,4-Dimethoxyquinoline

HRID 401237

Reaction equation

HRID 401237 reaction equation
Cl[C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O-:14].[Na+].[CH3:16][OH:17]>O>[CH3:13][O:14][C:2]1[CH:11]=[C:10]([O:17][CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6075032,4-DichloroquinolineHCID 10942334Sodium Methoxide

Product 1

HCID 1424362,4-Dimethoxyquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 2,4-dichloroquinoline in MeOH (100 mL) was added sodium methoxide (50 g). The mixture was heated at reflux for 2 days. After cooling, the mixture was filtered. The filtrate was concentrated under reduced pressure to yield a residue that was dissolved in water and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated to give 2,4-dimethoxyquinoline as a white solid (13 g, 74% over 2 steps).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 days
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto yield a residue that
  7. extractionextracted with CH2Cl2
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-84c763bce8b44f4e85babf6d86534c8a
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Linked notes

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