N-Methoxy-N-methylisonicotinamide → 2-Phenyl-1-(pyridin-4-yl)ethan-1-one

HRID 401169Notes

Reaction equation

HRID 401169 reaction equation
CON(C)[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.[CH2:13]([Mg]Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[C:14]1([CH2:13][C:4]([C:5]2[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=2)=[O:11])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 3817473N-Methoxy-N-methylisonicotinamideHCID 178418336HCID 178418336, compound

Product 1

HCID 110417042-Phenyl-1-(pyridin-4-yl)ethan-1-oneYield 10.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N-methylisonicotinamide (500 mg, 3.0 mmol) in anhydrous THF (10 mL) was added benzylmagnesium chloride (2 M in THF, 1.8 mL, 3.6 mmol) drop wise at −78° C. After being stirred at the temperature for 2 h, the reaction was quenched with NH4Cl aqueous solution, and extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE:EtOAc=5:1) to give Intermediate 35 (60 mg, yield 10%).

Workup

  1. customthe reaction was quenched with NH4Cl aqueous solution
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-3ed2dd47041f421591166d67f9402598
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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