Hydrochloric Acid → 1-(4-Chloro-pyridin-2-yl)-ethanone

HRID 651019Notes

Reaction equation

HRID 651019 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](C#N)[CH:3]=1.[CH3:10][Mg]I.Cl.[C:14](=[O:17])(O)[O-].[Na+]>C1C=CC=CC=1.CCOCC>[C:14]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1)(=[O:17])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 6933424-Chloro-2-pyridinecarbonitrileHCID 178418373HCID 178418373, compound

Product 1

HCID 130119861-(4-Chloro-pyridin-2-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4-chloro-2-pyridinecarbonitrile (5.35 g, 34.6 mmol) in benzene (50 ml) and ether (50 ml) cooled to 0° C. was added dropwise over 20 min a 2 M solution of MeMgI in ether (23 ml, 46.3 mmol). After 0.5 h, the mixture was allowed to warm to ambient temperature, and stirring continued for 2 h. The mixture was cooled to 0° C. and 2M aqueous HCl (100 ml) added. The mixture was made basic with saturated aqueous sodium bicarbonate (80 ml) and the organic layer separated and dried (MgSO4). After removal of solvent, the residue was purified by flash chromatography eluting with ethyl acetate/hexane (1:5) to afford 3.60 g (60%) of 2-acetyl-4′-chloropyiidine.

Workup

  1. waitcontinued for 2 h
  2. temperatureThe mixture was cooled to 0° C.
  3. customthe organic layer separated
  4. dry with materialdried (MgSO4)
  5. customAfter removal of solvent
  6. customthe residue was purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (1:5)
  8. customto afford 3.60 g (60%) of 2-acetyl-4′-chloropyiidine

Sources & evidence

ORD record
ord-8b96352d85904185a398d8c33cc8cc25
Source dataset
uspto-grants-2001_08
Patent number
US06277878B1

Reaction notes

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