Pyridine → HCID 87138614, Verbindung

HRID 41947

Reaktionsgleichung

Reaktionsgleichung von HRID 41947
COC1C=C2C(=CC=1OC)C(=O)CC2.Cl.[N+](C1C=CC(CNO)=CC=1)([O-])=O.N1C=CC=CC=1.[N+:34]([C:37]1[CH:59]=[CH:58][C:40]([CH2:41][O:42]/[N:43]=[C:44]2\[CH2:45]C[CH2:47][C:48]3[C:53]\2=[CH:52][C:51]([O:54][CH3:55])=[C:50]([O:56][CH3:57])[CH:49]=3)=[CH:39][CH:38]=1)([O-:36])=[O:35]>C(O)C.C(OCC)(=O)C.CCCCCC>[N+:34]([C:37]1[CH:59]=[CH:58][C:40]([CH2:41][O:42]/[N:43]=[C:44]2\[CH2:45][CH2:47][C:48]3[C:53]\2=[CH:52][C:51]([O:54][CH3:55])=[C:50]([O:56][CH3:57])[CH:49]=3)=[CH:39][CH:38]=1)([O-:36])=[O:35]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 750185,6-Dimethoxy-1-indanoneHCID 86662371(4-Nitrobenzyl)hydroxylamine hydrochlorideHCID 87138450(E)-6,7-dimethoxy-N-[(4-nitrophenyl)methoxy]-3,4-dihydro-2H-naphthalen-1-imine

Produkt 1

HCID 87138614HCID 87138614, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

5,6-Dimethoxy-1-indanone (104 mg, 0.54 mmol) was subjected to reaction with (4-nitrobenzyl)hydroxylamine hydrochloride (125 mg, 0.61 mmol) in ethanol (5 mL) and pyridine (0.7 mL, 9.03 mmol) under the same conditions as described for (E)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one O-4-nitrobenzyl oxime. Subjection of the material obtained on work up to flash chromatography (3:7 v/v ethyl acetate/hexane elution) afforded a ca. 3:1 mixture of the E- and Z-isomeric forms of the title compound (98 mg, 53%) as a pale-yellow crystalline solid, m.p. 139-144° C., Rf 0.3.

Aufarbeitung

  1. customafforded

Quellen und Nachweise

ORD-Eintrag
ord-c9949940468a48e7a9d9394619648779
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536157B2

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