Ethanol → (8E)-3-methoxy-8-[(4-nitrophenyl)methoxyimino]-6,7-dihydro-5H-naphthalen-2-ol

Reaktionsgleichung

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[CH:4][C:3]=1[O:13][CH3:14].Cl.[N+:16]([C:19]1[CH:27]=[CH:26]C(CNO)=[CH:21][CH:20]=1)([O-:18])=[O:17].[N:28]1C=CC=CC=1.[CH2:34]([OH:36])[CH3:35]>>[N+:16]([C:19]1[CH:27]=[CH:26][C:35]([CH2:34][O:36]/[N:28]=[C:9]2\[CH2:8][CH2:7][CH2:6][C:5]3[C:10]\2=[CH:11][C:2]([OH:1])=[C:3]([O:13][CH3:14])[CH:4]=3)=[CH:21][CH:20]=1)([O-:18])=[O:17]

Komponenten

Edukt 4

HCID 702Ethanol

HCID 1049Pyridine

HCID 3168407-Hydroxy-6-methoxy-1-tetralone

HCID 86662371(4-Nitrobenzyl)hydroxylamine hydrochloride

Produkt 1

HCID 87138499(8E)-3-methoxy-8-[(4-nitrophenyl)methoxyimino]-6,7-dihydro-5H-naphthalen-2-olAusbeute 55 %

Versuchsvorschrift

7-Hydroxy-6-methoxy-1-tetralone (105 mg, 0.55 mmol) was subjected to reaction with (4-nitrobenzyl)hydroxylamine hydrochloride (122 mg, 0.60 mmol) in ethanol (5 mL) and pyridine (0.5 mL, 6.45 mmol) under the same conditions as described for (E)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2R)-one O-4-nitrobenzyl oxime. The solid obtained on work up was recrystallised (isopropanol) to yield the title compound (103 mg, 55%) as off-white crystals, m.p. 125-127° C.