Kojic Acid → 5-Hydroxy-2-hydroxymethyl-1-methylpyrid-4-one

HRID 1977321Notes

Reaction equation

HRID 1977321 reaction equation
[CH3:1][NH2:2].[CH:3]1[C:8](=[O:9])[C:7]([OH:10])=[CH:6]O[C:4]=1[CH2:11][OH:12]>O>[OH:12][CH2:11][C:4]1[N:2]([CH3:1])[CH:6]=[C:7]([OH:10])[C:8](=[O:9])[CH:3]=1

Participants

4

Reactant 2

HCID 3840Kojic AcidHCID 6329Methylamine

Product 1

HCID 1296825-Hydroxy-2-hydroxymethyl-1-methylpyrid-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 40% methylamine in water is added to a solution of kojic acid dissolved in hot distilled water. The pH of this solution is adjusted to 9.8 by the addition of HCl solution. The mixture is kept under reflux overnight and then decolorized with activated charcoal. The solvent is removed under reduced pressure. The white product is obtained upon recrystallization from hot water.

Workup

  1. dissolutiondissolved
  2. distillationin hot distilled water
  3. additionThe pH of this solution is adjusted to 9.8 by the addition of HCl solution
  4. temperatureunder reflux overnight
  5. customThe solvent is removed under reduced pressure
  6. customThe white product is obtained upon recrystallization from hot water

Sources & evidence

ORD record
ord-6bd84b0b631b458cab6b84e28a00ecd3
Source dataset
uspto-grants-2001_05
Patent number
US06232340B1

Reaction notes

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