Hydrochloric Acid → 4-Pyridinone,3-OH-2-Me

HRID 566863Notes

Reaction equation

HRID 566863 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.Cl>[Pd].C(O)C>[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 313Hydrochloric AcidHCID 27264163-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONE

Product 1

HCID 3238144-Pyridinone,3-OH-2-MeYield 67.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.00 g (2.68 mmol) of 2-methyl-3-benzyloxypyridine-4(1H)-one of dimethylene xylitol compound is put into a mixture of 10 mL ethanol—2 mL H2O; then 0.08 g of Pd/C at 10% is added, and the pH of the solution is adjusted to pH=1 with a solution of concentrated HCl. The reaction medium is then subjected to catalytic hydrogenolysis under agitation at room temperature for 4 hours. At the end of this hydrogenolysis, the reaction medium is filtered. Then, 25 mL of water is added to the residue, and the solution is neutralized by addition of an aqueous solution of soda. The reaction medium is extracted with 2×20 mL of dichloromethane; the organic phases are collected, dried on sodium sulphate, filtered, and evaporated under reduced pressure; 509 mg (1.80 mmol) of 2-methyl-3-hydroxypyridine-4(1H)-one of dimethylene xylitol is isolated, which is pure at chromatographic and NMR analyses. Yield: 67%.

Workup

  1. filtrationAt the end of this hydrogenolysis, the reaction medium is filtered
  2. additionThen, 25 mL of water is added to the residue
  3. additionthe solution is neutralized by addition of an aqueous solution of soda
  4. extractionThe reaction medium is extracted with 2×20 mL of dichloromethane
  5. customthe organic phases are collected
  6. customdried on sodium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a03787d4a018453aa650efd075cc6330
Source dataset
uspto-grants-2001_01
Patent number
US06177409B1

Reaction notes

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