Methane → 3-Hydroxy-2-methyl-1-(propan-2-yl)pyridin-4(1H)-one

HRID 1741988Notes

Reaction equation

HRID 1741988 reaction equation
[OH:1][CH:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]=[C:3]1[CH3:9].[CH:10](N)([CH3:12])[CH3:11].C>O.CC(C)=O>[CH:10]([N:4]1[CH:5]=[CH:6][C:7](=[O:8])[C:2]([OH:1])=[C:3]1[CH3:9])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 297MethaneHCID 6363IsopropylamineHCID 666058152-Methyl-3-hydroxy-4-pyridone

Product 1

HCID 101301403-Hydroxy-2-methyl-1-(propan-2-yl)pyridin-4(1H)-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

1-Isopropyl-3-hydroxy-2-methylpyrid-4-one was prepared by refluxing 3-hydroxy-2-methylpyrid-4-one (Maltol) (10.0 g) with 3 equivalents of isopropylamine (99%) in 200 ml of water for 8 hours. Decolorizing charcoal was added after refluxing and the mixture was stirred for 0.5 hours. The mixture was then filtered through a medium frit filter containing 0.5 inches of Celite. The filtered solution was then concentrated in vacuo (rotary evaporator) to remove the water and excess amine, leaving a dark thick oil. The oil was then dissolved in minimal amounts of hot acetone and filtered (repeatedly) through a medium frit filter. Brownish crystals (product) remained on the frit and these were then washed (3X) with 1 ml portions of hot acetone to obtain white crystals. m.p. 239°-242 ° C.

Workup

  1. temperatureafter refluxing
  2. filtrationThe mixture was then filtered through a medium frit
  3. filtrationfilter
  4. additioncontaining 0.5 inches of Celite
  5. concentrationThe filtered solution was then concentrated in vacuo (rotary evaporator)
  6. customto remove the water and excess amine
  7. customleaving a dark thick oil
  8. filtrationfiltered (repeatedly) through a medium frit
  9. filtrationfilter
  10. washthese were then washed (3X) with 1 ml portions of hot acetone
  11. customto obtain white crystals

Sources & evidence

ORD record
ord-f42ceb4a8b6d4008b04b6fe30e438c13
Source dataset
uspto-grants-1994_08
Patent number
US05336482

Reaction notes

Loading…