Pyridine → 3'-fluoro-4'-hydroxyacetophenone-O-4-nitrobenzyloxime

HRID 41961Notes

Reaction equation

HRID 41961 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH3:10])[CH:5]=[CH:6][C:7]=1[OH:8].Cl.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([CH2:20][O:21][NH2:22])=[CH:18][CH:17]=1)([O-:15])=[O:14].N1C=CC=CC=1>C(O)C>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][O:21][N:22]=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([F:1])[CH:3]=2)[CH3:10])=[CH:23][CH:24]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)HCID 27373251-(3-Fluoro-4-hydroxyphenyl)ethan-1-one

Product 1

HCID 1363498393'-fluoro-4'-hydroxyacetophenone-O-4-nitrobenzyloxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3′-fluoro-4′-hydroxyacetophenone (0.063 g, 0.411 mmol), O-(4-nitrobenzyl)hydroxylamine hydrochloride (0.100 g, 0.491 mmol) and pyridine (0.13 ml, 1.61 mmol) in ethanol (5 ml) was stirred at reflux under nitrogen for 5h and cooled to room temperature. The solution was concentrated to a pale yellow oil which was diluted with dichloromethane/water. The resultant mixture was extracted with dichloromethane (×3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to an off-white solid. The crude product was purified by column chromatography (SiO2), eluting with 8:2 petrol/ethyl acetate, to give a 3′-fluoro-4′-hydroxyacetophenone-O-4-nitrobenzyloxime (CP9-132) as light yellow solid (0.081 g, 65%),

Workup

  1. concentrationThe solution was concentrated to a pale yellow oil which
  2. additionwas diluted with dichloromethane/water
  3. extractionThe resultant mixture was extracted with dichloromethane (×3)
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to an off-white solid
  8. customThe crude product was purified by column chromatography (SiO2)
  9. washeluting with 8:2 petrol/ethyl acetate

Sources & evidence

ORD record
ord-428838e03eb742dda3e73b743666b1ff
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Reaction notes

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