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

HRID 1036643Notes

Reaction equation

HRID 1036643 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 before leaving the medium to stir at ambient temperature for 3 h. The ethanol is subsequently evaporated 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 and then the aqueous phase is extracted 5 times with 150 ml of ethyl acetate. The organic phases are subsequently combined, dried over sodium sulphate and concentrated under vacuum. 7.82 g of compound are obtained.

Workup

  1. custombefore leaving the medium
  2. customThe ethanol is subsequently evaporated under vacuum
  3. customthe residue obtained
  4. customThe organic phase is separated
  5. extractionthe aqueous phase is extracted 5 times with 150 ml of ethyl acetate
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b328686ab15c4290b20d187bf64ad43c
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

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