Methanol → (2,6-Dimethylquinolin-4-yl)methanol

HRID 1788372Notes

Reaction equation

HRID 1788372 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[N:3]=1.[NH4+].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O.[CH3:25][OH:26].S(=O)(=O)(O)O>O>[CH3:1][C:2]1[CH:11]=[C:10]([CH2:25][OH:26])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 134142,6-DimethylquinolineHCID 62648Ammonium Persulfate

Product 1

HCID 23018001(2,6-Dimethylquinolin-4-yl)methanolYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 10.0 g (63.6 mmol) of 2,6-dimethylquinoline and 29.1 g (127.5 mmol) of ammonium peroxodisulfate in a mixed solvent of methanol (140 mL)-water (110 mL) was added 4.0 mL of concentrated sulfuric acid and heated under reflux for 24 hours. After the reaction mixture was left to cool, methanol was evaporated under a reduced pressure. The remaining solution was adjusted to pH 10 by adding sodium carbonate, and then extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was removed. The obtained residue was purified by column chromatography (silica gel 200 g, developing solvent: chloroform:ethyl acetate:triethyamine=1:1:0.01) to obtain 5.50 g (yield 46%) of (2,6-dimethylquinolin-4-yl)methanol. Its physical properties are shown below.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. waitAfter the reaction mixture was left
  4. temperatureto cool
  5. custommethanol was evaporated under a reduced pressure
  6. additionby adding sodium carbonate
  7. extractionextracted with chloroform
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed
  11. customThe obtained residue was purified by column chromatography (silica gel 200 g, developing solvent: chloroform:ethyl acetate:triethyamine=1:1:0.01)

Sources & evidence

ORD record
ord-b370c6950ceb406cb4e529876c96c623
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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