Hydrochloric Acid → Ethyl 2-acetylnicotinate

HRID 539700Notes

Reaction equation

HRID 539700 reaction equation
C([O:3][C:4]([C:6]1[N:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH2:5])C.Cl>CC(C)=O>[C:4]([C:6]1[N:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:3])[CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86680868Ethyl 2-(1-ethoxyvinyl)nicotinate

Product 1

HCID 86680869Ethyl 2-acetylnicotinateYield 63.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of ethyl 2-(1-ethoxyvinyl)nicotinate (27 g) and acetone (300 mL) was added 2M hydrochloric acid (370 mL), and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, to the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (15 g).

Workup

  1. customThe solvent was evaporated under reduced pressure, to the residue
  2. additionwere added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7394fffee2824ee3a530f55ef55d5aba
Source dataset
uspto-grants-2014_10
Patent number
US08871766B2

Reaction notes

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