Ammonia → 3-Ethoxy-2-methylpyridin-4(1H)-one

HRID 912654Notes

Reaction equation

HRID 912654 reaction equation
[NH3:1].[CH2:2]([O:4][C:5]1[C:10](=[O:11])[CH:9]=[CH:8]O[C:6]=1[CH3:12])[CH3:3]>C(O)C>[CH2:2]([O:4][C:5]1[C:10](=[O:11])[CH:9]=[CH:8][NH:1][C:6]=1[CH3:12])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 98340133-Ethoxy-2-methyl-4H-pyran-4-one

Product 1

HCID 674147653-Ethoxy-2-methylpyridin-4(1H)-oneYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ammonia (28% aq. 20 mL) was added to a solution of 3-ethoxy-2-methyl-4H-pyran-4-one (8.5 g, 55 mmol, obtained from Example 4(a)) in ethanol (20 mL) and the mixture was stirred under reflux for 24 h. The reaction mixture was cooled to r.t. and the solution was evaporated in vacuo. The pH was adjusted to pH 1 with 2M HCl, and the aqueous phase was extracted with ethyl acetate. The pH of the water phase was then adjusted to pH 10 with 2M sodium hydroxide. The aqueous phase was extracted with ethyl acetate (3×100 mL) and then saturated with NaCl (s) and extracted with CHCl3. The organic phase was dried (Na2SO4) and evaporated to give the title product (8.0 g, 95%). The crude product was used in the next step without further purification.

Workup

  1. temperatureunder reflux for 24 h
  2. customthe solution was evaporated in vacuo
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. extractionThe aqueous phase was extracted with ethyl acetate (3×100 mL)
  5. extractionsaturated with NaCl (s) and extracted with CHCl3
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-fe112101d61a476ab51ca2fdee7da770
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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