Ethanol → 4-Pyridinone,3-OH-2-Me

HRID 566862Notes

Reaction equation

HRID 566862 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6](=[O:16])[C:7]=1[O:8]CC1C=CC=CC=1.C(O)C>[Pd].OCC(CO)O>[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6](=[O:16])[C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 702EthanolHCID 27264163-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONE

Product 1

HCID 3238144-Pyridinone,3-OH-2-MeYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 753GlycerolSolvent2×

Procedure

4.2 g (14.5 mmol) of 2-methyl-3-benzyloxypyridine-4(1H)-one of glycerol is put into the mixture of 54 mL ethanol—6 mL H2O, and 0.11 g of Pd/C at 10% is added. The reaction medium is subjected to catalytic hydrogenolysis under agitation at room temperature for 24 hours. At the end of this hydrogenolysis, the reaction medium is filtered. The filtered Pd/C is washed with EtOH; then the filtrate is evaporated under reduced pressure. The solid residue is re-crystallized in a MeOH-ethyl acetate mixture to obtain 2.05 g (10.3 mmol) of 2-methyl-3-hydroxypyridine-4(1H)-one of glycerol, which is pure at chromatographic and NMR analyses. Yield: 71%.

Workup

  1. additionis added
  2. filtrationAt the end of this hydrogenolysis, the reaction medium is filtered
  3. washThe filtered Pd/C is washed with EtOH
  4. customthen the filtrate is evaporated under reduced pressure
  5. customThe solid residue is re-crystallized in a MeOH-ethyl acetate mixture

Sources & evidence

ORD record
ord-2d9813b6a75a4236958be0b7c47b6c44
Source dataset
uspto-grants-2001_01
Patent number
US06177409B1

Reaction notes

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