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

HRID 41961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41961
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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%),

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-428838e03eb742dda3e73b743666b1ff
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536157B2

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