Methane → 1-Ethyl-2-methyl-3-hydroxypyridin-4-one

HRID 1741989Notes

Reaction equation

HRID 1741989 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5]O[C:3]=1[CH3:9].[CH2:10]([NH2:12])[CH3:11].C>O>[CH2:10]([N:12]1[CH:5]=[CH:6][C:7](=[O:8])[C:2]([OH:1])=[C:3]1[CH3:9])[CH3:11]

Participants

5

Reactant 3

HCID 297MethaneHCID 6341EthylamineHCID 8369Maltol

Product 1

HCID 944131-Ethyl-2-methyl-3-hydroxypyridin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Ethyl-3-hydroxy-2-methylpyrid-4-one was prepared by dissolving 10.0 g of 3-hydroxy-2-methylpyr-4-one (Maltol) and 3 equivalents of ethylamine (70%) in 200 ml of water. The reaction mixture was refluxed for 10 hours at which time it was black in color. Decolorizing charcoal was then added to the mixture and it was stirred an additional 0.5 hours. The mixture was then filtered through a fine frit and the filtrate was concentrated in vacuo to remove the water and excess amine. The resulting brown crystals were recrystallized using hot methanol which yielded white needles of pure product. m.p. 204°-205 ° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 10 hours at which time it
  2. filtrationThe mixture was then filtered through a fine frit
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto remove the water and excess amine
  5. customThe resulting brown crystals were recrystallized
  6. customyielded white needles of pure product

Sources & evidence

ORD record
ord-b53991ea868e406eb52da3db051dd73c
Source dataset
uspto-grants-1994_08
Patent number
US05336482

Reaction notes

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