Ethanol → (E)-6,7-dimethoxy-N-[(4-nitrophenyl)methoxy]-3,4-dihydro-2H-naphthalen-1-imine

HRID 41946

Reaktionsgleichung

Reaktionsgleichung von HRID 41946
Cl.[N+:2]([C:5]1[CH:13]=[CH:12]C(CNO)=[CH:7][CH:6]=1)([O-:4])=[O:3].[N:14]1C=CC=CC=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:31]=1[O:32][CH3:33])[C:28](=O)[CH2:27][CH2:26][CH2:25]2.[CH2:35]([OH:37])[CH3:36]>>[N+:2]([C:5]1[CH:13]=[CH:12][C:36]([CH2:35][O:37]/[N:14]=[C:28]2\[CH2:27][CH2:26][CH2:25][C:24]3[C:29]\2=[CH:30][C:31]([O:32][CH3:33])=[C:22]([O:21][CH3:20])[CH:23]=3)=[CH:7][CH:6]=1)([O-:4])=[O:3]

Komponenten

5

Edukt 4

HCID 702EthanolHCID 1049PyridineHCID 2668163,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenoneHCID 86662371(4-Nitrobenzyl)hydroxylamine hydrochloride

Produkt 1

HCID 87138450(E)-6,7-dimethoxy-N-[(4-nitrophenyl)methoxy]-3,4-dihydro-2H-naphthalen-1-imineAusbeute 86 %

Versuchsvorschrift

(4-Nitrobenzyl)hydroxylamine hydrochloride (119 mg, 0.58 mmol) and pyridine (0.5 mL, 6.45 mmol) were added to a magnetically stirred solution of 6,7-dimethoxy-1-tetralone (100 mg, 0.48 mmol) in ethanol (2 mL) and the ensuing mixture heated at reflux for 2 h. The cooled reaction mixture was concentrated under reduced pressure and the residue thus obtained partitioned between CH2Cl2 (5 mL) and water (5 mL). The separated aqueous layer was washed with CH2Cl2 (1×5 mL) and the combined organic extracts were then dried (MgSO4), filtered and concentrated under reduced pressure. The ensuing residue was subjected to flash chromatography (3:7 v/v ethyl acetate/hexane elution) and concentration of the appropriate fractions gave the title compound (148 mg, 86%) as yellow crystals, m.p. 124-127° C., Rf 0.3.

Aufarbeitung

  1. temperaturethe ensuing mixture heated
  2. temperatureat reflux for 2 h
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue thus obtained
  6. custompartitioned between CH2Cl2 (5 mL) and water (5 mL)
  7. washThe separated aqueous layer was washed with CH2Cl2 (1×5 mL)
  8. dry with materialthe combined organic extracts were then dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. washThe ensuing residue was subjected to flash chromatography (3:7 v/v ethyl acetate/hexane elution) and concentration of the appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-c09895e95432408b84d3160e9fa622e7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536157B2

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