Methane → Deferiprone

HRID 481462Notes

Reaction equation

HRID 481462 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5]O[C:3]=1[CH3:9].[CH3:10][NH2:11].C>O>[CH3:10][N:11]1[CH:5]=[CH:6][C:7](=[O:8])[C:2]([OH:1])=[C:3]1[CH3:9]

Participants

5

Reactant 3

HCID 297MethaneHCID 6329MethylamineHCID 8369Maltol

Product 1

HCID 2972Deferiprone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In particular, 3-hydroxy-2-methyl-4-pyrone (10 g) was refluxed for 6.5 hours with three equivalents of aqueous methylamine (40%) in 200 ml of water. The reaction mixture was allowed to cool after which decolorizing charcoal was added to the solution, and the mixture was stirred for 0.5 hours. After filtration, the solvent was evaporated under reduced pressure, and the solid residue recrystallized three times from water to yield 1,2-dimethyl-3-hydroxypyrid-4-one (HK-1, L1, CP20, DMHP) as fine white needles.

Workup

  1. temperatureto cool after which
  2. additionwas added to the solution
  3. filtrationAfter filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customthe solid residue recrystallized three times from water

Sources & evidence

ORD record
ord-b936506633274afa9738a21e76e656ef
Source dataset
uspto-grants-1998_08
Patent number
US05789426

Reaction notes

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