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

HRID 396437Notes

Reaction equation

HRID 396437 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)-ethanoneYield 60%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4-chloro-2-pyridinecarbonitrile (5.35 g, 38.6 mmol) in benzene (50 ml) and ether (50 ml) cooled to 0° C. was added dropwise over 20 min a 2M 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-chloropyridine.

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)

Sources & evidence

ORD record
ord-54c5df0661cf42e9a2f0b76b507c5e8c
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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