Hydrochloric Acid → 1-[2-(4-Fluorophenyl)pyridin-4-yl]ethanone

HRID 1026758Notes

Reaction equation

HRID 1026758 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([C:17]#N)[CH:14]=[CH:13][N:12]=2)=[CH:7][CH:6]=1.Cl.[OH-:20].[Na+]>C(OCC)C.C(OCC)(=O)C>[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([C:17](=[O:20])[CH3:1])[CH:14]=[CH:13][N:12]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 463120752-(4-Fluorophenyl)isonicotinonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 866904831-[2-(4-Fluorophenyl)pyridin-4-yl]ethanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methylmagnesium bromide (1.85 g) was added to a suspension of 2-(4-fluorophenyl)pyridine-4-carbonitrile (1.0 g) in diethyl ether (10 mL), and the mixture was stirred at room temperature overnight. After adding ice and 2M hydrochloric acid and stirring, the resulting mixture was made basic with 2M aqueous sodium hydroxide solution. After exracting with ethyl acetate, the organic phase was separated out and the solvent was distilled off The resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=98:2-80:20) to afford 1-[2-(4-fluorophenyl)pyridin-4-yl]ethanone (350 mg).

Workup

  1. stirringstirring
  2. customthe organic phase was separated out
  3. distillationthe solvent was distilled off The resulting residue
  4. customwas purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=98:2-80:20)

Sources & evidence

ORD record
ord-15c8269532ba4678b81e80489a24a818
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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