Methanol → HCID 23017958, compound

HRID 1788398Notes

Reaction equation

HRID 1788398 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:17])[CH:13]=[CH:12]2.[NH4+].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O.[OH2:30].[CH3:31]O>>[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:17])[CH:13]=[C:12]2[CH2:31][OH:30]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 62648Ammonium PersulfateHCID 112406548-Fluoro-2-methylquinoline

Product 1

HCID 23017958HCID 23017958, compoundYield 32%

Procedure

Concentrated sulfuric acid (1.2 mL) was added to a solution of 2.70 g (16.8 mmol) of 8-fluoro-2-methylquinoline and 7.70 g (33.7 mmol) of ammonium peroxodisulfate in a mixture of methanol (35 mL)-water (25 mL) and heated under reflux for 15 hours. The reaction mixture was left to cool, followed by a removal of methanol under a reduced pressure. Sodium carbonate was added to the residue to adjust its pH to 10, and then the mixture was 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 washed with ether to obtain 1.03 g (yield 32%) of (8-fluoro-2-methylquinolin-4-yl)methanol. Its physical properties are shown below.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hours
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. customfollowed by a removal of methanol under a reduced pressure
  6. additionSodium carbonate was added to the residue
  7. extractionthe mixture was extracted 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. washThe obtained residue was washed with ether

Sources & evidence

ORD record
ord-7b407a8250b7486dbbb86d1adc1d85a8
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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