Hydrochloric Acid → N-(5-acetylpyridin-3-yl)acetamide

HRID 1712919Notes

Reaction equation

HRID 1712919 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[N:10][CH:11]=1)=[CH2:5])C.Cl.C([O-])(O)=O.[Na+]>CC(C)=O>[C:4]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[N:10][CH:11]=1)(=[O:3])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59463096N-[5-(1-ethoxyvinyl)pyridin-3-yl]acetamide

Product 1

HCID 59463126N-(5-acetylpyridin-3-yl)acetamideYield 42.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-[5-(1-ethoxyvinyl)pyridin-3-yl]acetamide (2.4 mmol) in acetone (9 mL) was added 1N HCl (1 mL). The reaction mixture was allowed to stir at rt overnight and then basified with sat NaHCO3 and extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give N-(5-acetylpyridin-3-yl)acetamide (0.180 g, 42%) as a white solid. LCMS: (FA) ES+ 179.1.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-656848e6eb94422299f0f751b9247ddd
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

Loading…