Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1) → (E)-1-(4-methoxy-3-propan-2-yloxyphenyl)-N-[(4-nitrophenyl)methoxy]ethanimine

HRID 41929

Reaktionsgleichung

Reaktionsgleichung von HRID 41929
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:13](=O)[CH3:14])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:3])[CH3:2].Cl.[N+:17]([C:20]1[CH:28]=[CH:27][C:23]([CH2:24][O:25][NH2:26])=[CH:22][CH:21]=1)([O-:19])=[O:18]>>[N+:17]([C:20]1[CH:21]=[CH:22][C:23]([CH2:24][O:25]/[N:26]=[C:13](/[C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:6]=2)\[CH3:14])=[CH:27][CH:28]=1)([O-:19])=[O:18]

Komponenten

3

Edukt 2

HCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)HCID 201606221-(4-Methoxy-3-(propan-2-yloxy)phenyl)ethan-1-one

Produkt 1

HCID 25100405(E)-1-(4-methoxy-3-propan-2-yloxyphenyl)-N-[(4-nitrophenyl)methoxy]ethanimineAusbeute 89 %

Versuchsvorschrift

3′-Isopropoxy-4′-methoxyacetophenone (8) (150 mg, 0.720 mmol) was condensed with compound 19 (162 mg, 0.792 mmol) according to the general procedure II-A defined above. After being heated for 3 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing yellow oil was dissolved in CH2Cl2 (20 mL) and the resulting solution washed with H2O (2×15 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (15:85 v/v ethyl acetate/hexane elution) to afford the title compound CP30254 (229 mg, 89%) as a pale-yellow oil, which solidified upon extensive standing, m.p. 44.5-46.1° C., Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

Aufarbeitung

  1. temperatureAfter being heated for 3 h the reaction mixture
  2. temperaturewas cooled
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe ensuing yellow oil was dissolved in CH2Cl2 (20 mL)
  5. washthe resulting solution washed with H2O (2×15 mL)
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe oil thus obtained
  10. washwas subjected to flash chromatography (15:85 v/v ethyl acetate/hexane elution)

Quellen und Nachweise

ORD-Eintrag
ord-cd340fc503744b1facca5e0514a2ef39
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536157B2

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