Methanol → Methyl 8-hydroxyquinoline-5-carboxylate

HRID 1795750Notes

Reaction equation

HRID 1795750 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:20]O>>[OH:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]([O:14][CH3:20])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4596178-Hydroxy-5-quinolinecarboxylic acid

Product 1

HCID 22179176Methyl 8-hydroxyquinoline-5-carboxylate

Procedure

16.25 g (86 mmol) of 8-hydroxy-5-quinolinecarboxylic acid were dissolved in 70 ml of methanol, 3 ml of concentrated sulfuric acid were added and the mixture was heated under reflux for 25 hours. The solvent was then removed and the residue was taken up in ice-water, adjusted to a pH of 8 using sodium carbonate solution and filtered hot. The residue was extracted with methyl-tert-butyl ether for 7 hours on a jacketed Soxhlet extractor, and the solvent was subsequently removed from the extract. This gave 6.8 g of a brown powder;

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 25 hours
  3. customThe solvent was then removed
  4. filtrationfiltered hot
  5. extractionThe residue was extracted with methyl-tert-butyl ether for 7 hours on a jacketed Soxhlet extractor
  6. customthe solvent was subsequently removed from the extract

Sources & evidence

ORD record
ord-c2555718e01c42f59978855123c40864
Source dataset
uspto-grants-2006_04
Patent number
US07030063B1

Reaction notes

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