Ethanol → (E)-2-(3-bromo-alpha-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridine

HRID 442731Notes

Reaction equation

HRID 442731 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[C:5]([C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=1)=O.Cl.[C:19]([O:23][NH2:24])([CH3:22])([CH3:21])[CH3:20].C(O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])/[C:5](/[C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=1)=[N:24]\[O:23][C:19]([CH3:22])([CH3:21])[CH3:20].[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])/[C:5](/[C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=1)=[N:24]/[O:23][C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 702EthanolHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 539533172-(3-Bromo-4-fluorobenzoyl)-3-hydroxypyridine

Product 2

HCID 135494341(E)-2-(3-bromo-alpha-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridineHCID 136340705(Z)-2-(3-bromo-alpha-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(3-bromo-4-fluorobenzoyl)-3-hydroxypyridine (1.26 g), O-t-butylhydroxylamine hydrochloride (1.08 g) and ethanol (10 mL) was refluxed for 2 hours. The reaction mixture was poured into water, and subjected to extraction with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate), followed by evaporating the solvent under reduced pressure. The residue was subjected to purification by means of a silica gel column (ethyl acetate--hexane) to afford (E)-2-(3-bromo-α-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridine (0.89 g) and (Z)-2-(3-bromo-α-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridine (0.51 g) (compounds 17 and 16).

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
  5. customby evaporating the solvent under reduced pressure
  6. customThe residue was subjected to purification by means of a silica gel column (ethyl acetate--hexane)

Sources & evidence

ORD record
ord-990e19638bed4bf483a8f5785f519514
Source dataset
uspto-grants-1999_04
Patent number
US05891895

Reaction notes

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