Hydrochloric Acid → 1-(3-Chloropyridin-2-yl)ethanone

HRID 968627Notes

Reaction equation

HRID 968627 reaction equation
[Cl:1][C:2]1C(C#N)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:10][Mg]I.C([O:15][CH2:16][CH3:17])C.Cl>C1COCC1>[C:16]([C:17]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=1)(=[O:15])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8182583-Chloropyridine-2-carbonitrileHCID 178418373HCID 178418373, compound

Product 1

HCID 146449721-(3-Chloropyridin-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-chloro-2-cyanopyridine (10.0 g, 0.072 mol, Chem. Pharm. Bull. (1985) 33:565–571) in anhydrous THF (200 mL) under N2 atmosphere and cool in an ice bath. Add drop wise 3.0 M MeMgI in diethyl ether (48 ml, 0.14 mol) to the reaction mixture and stir in an ice bath for 2 hours. Pour the reaction mixture over ice cold water, acidify the mixture with 2.0 N aq. HCl to pH 2 to 3. Extract the reaction mixture with EtOAc (3×100 mL) and dry over anhydrous MgSO4. Filter, concentrate under vacuum and then filter through a pad of silica gel using 20% ethyl acetate/hexane as eluent. Removal of solvent under reduced pressure gives pure 2-acetyl-3-chloropyridine as oil.

Workup

  1. temperaturecool in an ice bath
  2. additionPour the reaction mixture over ice cold water
  3. extractionExtract the reaction mixture with EtOAc (3×100 mL)
  4. dry with materialdry over anhydrous MgSO4
  5. filtrationFilter
  6. concentrationconcentrate under vacuum
  7. filtrationfilter through a pad of silica gel using 20% ethyl acetate/hexane as eluent
  8. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-52b0ec541f2f4104a5395735b1903a6f
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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