Hydrochloric Acid → 4-Hydroxy-1-Methyl-1h-pyridin-2-one

HRID 1416189Notes

Reaction equation

HRID 1416189 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.S(OC)(O[CH3:13])(=O)=O.Cl>[OH-].[Na+]>[OH:8][C:6]1[CH:5]=[CH:4][N:3]([CH3:13])[C:2](=[O:1])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 178516518HCID 178516518, compound

Product 1

HCID 546845234-Hydroxy-1-Methyl-1h-pyridin-2-oneYield 22.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2,4-Dihydroxypyridine (3.0 g) was dissolved in 2N aqueous sodium hydroxide solution (30 ml) and dimethyl sulphate (3.7 g) was added dropwise over 90 minutes. The mixture was stirred at room temperature overnight, acidified with concentrated hydrochloric acid, the solvent removed under reduced pressure, the residue stirred in 5% methanol/dichloromethane and filtered. The filtrate was evaporated and the crude product was chromatographed on silica using 7:93 methanol: dichloromethane as the eluent to yield 1,2-dihydro-4-hydroxy-1-methyl-2-oxopyridine (0.77 g) as a yellow solid. m.p. 165-169° C. Found: C,57.28; H,5.47; N,10.89. C6H7NO2 requires C,57.59; H,5.64; N,11.19%.

Workup

  1. customthe solvent removed under reduced pressure
  2. stirringthe residue stirred in 5% methanol/dichloromethane
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe crude product was chromatographed on silica using 7:93 methanol

Sources & evidence

ORD record
ord-54e4f9f6404a445cae9caaa153ae5acd
Source dataset
uspto-grants-1999_06
Patent number
US05912244

Reaction notes

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