Potassium bisulfate → 1-(2-Chloropyridin-4-yl)ethan-1-one

HRID 1635513Notes

Reaction equation

HRID 1635513 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:10]=[C:9]([C:11](=[O:16])N(C)OC)[CH:8]=[CH:7][N:6]=1.S([O-])(O)(=O)=O.[K+]>C1COCC1.O>[Cl:4][C:5]1[CH:10]=[C:9]([C:11](=[O:16])[CH3:1])[CH:8]=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 185068942-Chloro-N-methoxy-N-methylisonicotinamideHCID 178418573HCID 178418573, compound

Product 1

HCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To methylmagnesium bromide (30 mL of 3.0 M in THF) was added a solution of 2-chloro-4-(N-methyl-N-methoxycarbamoyl)pyridine (6.0 g, 0.03 mol) in 20 mL of THF at 0 C. The reaction mixture was stirred overnight while allowing to warm up to room temperature. A solution of potassium hydrogensulfate (12 g) in 300 mL of water was added and the aqueous phase was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated 4.0 g (86%) of product as a yellow oil. This was used in next step without purification.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated 4.0 g (86%) of product as a yellow oil
  6. customThis was used in next step without purification

Sources & evidence

ORD record
ord-c55721e99f964473b149231d6b58e39e
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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