Ammonia → 3-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONE

HRID 920679Notes

Reaction equation

HRID 920679 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:17].[OH-].[Na+].[Cl-].[NH4+]>C(O)C.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][NH:17][C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 27264163-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONEYield 43%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

The compound 2 (162.2 g, 750 mmol) was dissolved in ethanol (487 ml), and aqueous ammonia (28%, 974 ml) and a 6N aqueous sodium hydroxide solution (150 ml, 900 mmol) were added. After the reaction solution was stirred at 90° C. for 1 hour, this was cooled to under ice-cooling, and ammonium chloride (58 g, 1080 mmol) was added. To the reaction solution was added chloroform, this was extracted, and the organic layer was washed with an aqueous saturated sodium bicarbonate solution, and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, isopropyl alcohol and diethyl ether were added to the residue, and precipitated crystals were filtered to obtain 3-benzyloxy-2-methyl-1H-pyridine-4-one 3 (69.1 g, 43%) as a pale yellow crystal.

Workup

  1. temperaturethis was cooled to under ice-
  2. temperaturecooling
  3. extractionthis was extracted
  4. washthe organic layer was washed with an aqueous saturated sodium bicarbonate solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure, isopropyl alcohol and diethyl ether
  7. additionwere added to the residue
  8. customprecipitated crystals
  9. filtrationwere filtered

Sources & evidence

ORD record
ord-2650c066cbf54386a2cce1ccafe038d7
Source dataset
uspto-grants-2016_03
Patent number
US09273065B2

Reaction notes

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