Ethanol → 2-(4-bromopyridin-2-yl)-1-(4-fluorophenyl)ethanone Oxime

HRID 1190857Notes

Reaction equation

HRID 1190857 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=O)[CH:3]=1.C(O)C.N1C=CC=CC=1.Cl.[NH2:28][OH:29]>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:28][OH:29])[CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 672466172-(4-Bromopyridin-2-yl)-1-(4-fluorophenyl)ethanone

Product 1

HCID 866713742-(4-bromopyridin-2-yl)-1-(4-fluorophenyl)ethanone OximeYield 104.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.5 g (24.26 mmol) of 2-(4-bromopyridin-2-yl)-1-(4-fluorophenyl)ethanone are placed in a round-bottomed flask containing 100 mL of absolute ethanol. 20 mL (247.78 mmol) of pyridine and 7.08 g (101.88 mmol) of hydroxylamine monohydrochloride are added, and the medium is then stirred for 3 hours at room temperature. The ethanol is then evaporated off under vacuum and the residue obtained is taken up in 250 mL of water and 250 mL of ethyl acetate. The organic phase is separated out and the aqueous phase is then extracted 5 times with 150 mL of ethyl acetate. The organic phases are then combined, dried over sodium sulfate and concentrated under vacuum. 7.82 g of compound are obtained.

Workup

  1. customThe ethanol is then evaporated off under vacuum
  2. customthe residue obtained
  3. customThe organic phase is separated out
  4. extractionthe aqueous phase is then extracted 5 times with 150 mL of ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a19f904a0d514eb9b75f3363a468b31c
Source dataset
uspto-grants-2014_03
Patent number
US08680096B2

Reaction notes

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