6-(1-Ethoxy-vinyl)-nicotinonitrile → 6-Acetylnicotinonitrile

HRID 1191088Notes

Reaction equation

HRID 1191088 reaction equation
C([O:3][C:4]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)=[CH2:5])C>C1COCC1.Cl>[C:4]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)(=[O:3])[CH3:5]

Participants

4

Reactant 1

HCID 598289076-(1-Ethoxy-vinyl)-nicotinonitrile

Product 1

HCID 231037476-AcetylnicotinonitrileYield 65%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve crude 6-(1-ethoxy-vinyl)-nicotinonitrile (14.5 g, ca. 80%) in THF (120 mL) and 2.5 N hydrochloric acid (40 mL). Stir the solution for 16 h at room temperature. Quench the reaction with saturated aqueous NaHCO3 (pH to 7.5). Extract the mixture with EtOAc (200 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (120 g) eluting with hexane/EtOAc (9:1 to 3:1 gradient) to obtain the desired intermediate (4.2 g, 65%).

Workup

  1. customQuench
  2. customthe reaction with saturated aqueous NaHCO3 (pH to 7.5)
  3. extractionExtract the mixture with EtOAc (200 mL)
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the crude mixture by chromatography on silica gel (120 g)
  8. washeluting with hexane/EtOAc (9:1 to 3:1 gradient)

Sources & evidence

ORD record
ord-043f941978734a08bbbf6fdd381112ed
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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