Sodium Acetate → HCID 15858883, compound

HRID 394672Notes

Reaction equation

HRID 394672 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][CH2:12][C:13]#[N:14].[C:15]([O-])(=[O:17])[CH3:16].[Na+].[H][H]>[Ni].C(OC(=O)C)(=O)C.O>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16]

Participants

7

Reactant 3

HCID 517045Sodium AcetateHCID 12761751HCID 12761751, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15858883HCID 15858883, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

0.53 g (2.82 mmol) of the nitrile obtained in Step D is added to a suspension of 0.25 g (4.23 mmol) of Raney nickel and 0.34 g (4.23 mmol) of sodium acetate in 8 ml of acetic anhydride. The reaction mixture is subjected to hydrogen pressure of 50 psi at 50° C. for 6 hours. The remaining catalyst is then filtered off over Celite; the solvent is then evaporated in vacuo. The residue obtained is taken up in water; the reaction medium is then extracted with ethyl acetate. The organic phase is washed with a saturated solution of sodium hydrogen carbonate and then dried over magnesium sulphate. After filtration and evaporation of the solvent under reduced pressure, the residue obtained is purified on a silica column (eluant: ethyl acetate) to result in the title amide in the form of a clear syrup.

Workup

  1. filtrationThe remaining catalyst is then filtered off over Celite
  2. customthe solvent is then evaporated in vacuo
  3. customThe residue obtained
  4. extractionthe reaction medium is then extracted with ethyl acetate
  5. washThe organic phase is washed with a saturated solution of sodium hydrogen carbonate
  6. dry with materialdried over magnesium sulphate
  7. filtrationAfter filtration and evaporation of the solvent under reduced pressure
  8. customthe residue obtained
  9. customis purified on a silica column (eluant: ethyl acetate)

Sources & evidence

ORD record
ord-669f46c61d0b455db03a7605534b9c19
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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