Ammonia → 2-Methyl-3-(phenylmethoxy)-4(3H)-pyridinone

HRID 350647Notes

Reaction equation

HRID 350647 reaction equation
[NH3:1].[CH2:2]([O:9][C:10]1[C:15](=[O:16])[CH:14]=[CH:13]O[C:11]=1[CH3:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[CH2:2]([O:9][CH:10]1[C:15](=[O:16])[CH:14]=[CH:13][N:1]=[C:11]1[CH3:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 693437942-Methyl-3-(phenylmethoxy)-4(3H)-pyridinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

28% aqueous ammonia (100 ml) and 30 ml of ethanol were added to 3-benzyloxy-2-methyl-4-pyrone (40.6 g, 0.188 mol). The mixture was stirred at room temperature for 5 days. The reaction mixture was concentrated under the reduced pressure. The precipitate was filtered, and was then washed with a minor amount of ethyl acetate to give 32.2 g of 3-benzyloxy-2-methyl-4-pyridone as a light yellow crystal. The same compound was also obtained from the filtrate (5.6 g, yield 93%).

Workup

  1. concentrationThe reaction mixture was concentrated under the reduced pressure
  2. filtrationThe precipitate was filtered
  3. washwas then washed with a minor amount of ethyl acetate

Sources & evidence

ORD record
ord-b6e6b19f184240c9a58a1a91aad130b7
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

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