Hydrochloric Acid → 1-[6-(Difluoromethoxy)pyridin-3-yl]ethan-1-one

HRID 1690177Notes

Reaction equation

HRID 1690177 reaction equation
CON(C)C(=O)[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:11][CH:12]([F:14])[F:13].[CH3:17][Mg]Br.Cl.[C:21](=[O:24])([O-])O.[Na+]>O1CCCC1>[F:14][CH:12]([F:13])[O:11][C:6]1[CH:5]=[CH:10][C:9]([C:21](=[O:24])[CH3:17])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 866394092-(Difluoromethoxy)-N-methoxy-N-methyl-3-pyridinecarboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 669048941-[6-(Difluoromethoxy)pyridin-3-yl]ethan-1-oneYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-methoxy-N-methyl-2-difluoromethoxynicotinamide (336 mg, 1.45 mmol) was dissolved in tetrahydrofuran (7.3 mL). 0.93 M methylmagnesium bromide (2.4 mL, 2.18 mmol) was added dripwise at 0° C. under an argon atmosphere. The resultant mixture was stirred for 10 minutes and added with 1N hydrochloric acid at the same temperature. Subsequently, the reaction solution was added with a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified using silica-gel column chromatography (n-hexane/ethyl acetate=4/1). 1-(2-(Difluoromethoxy)pyridin-5-yl)ethanone (264 mg, yield 98%) was obtained as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified

Sources & evidence

ORD record
ord-425253f52f42453287381bed101c7997
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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