Reaktion #70231

Reaktionsgleichung

(E)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one O-4-nitrobenzyl oxime

7-Hydroxy-6-methoxy-1-tetralone

O-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)hydroxylamine hydrochloride

pyridine

→

title compound

Ausbeute 9.0%

(E)-7-Hydroxy-6-methoxy-3,4-dihydronaphthalen-1(2H)-one O-benzo[c][1,2,5]oxadiazol-5-ylmethyl oxime

Ausbeute 9.0%

Lösungsmittel

ethanol

ethyl acetate hexane

Reaktionsbedingungen

Vorschrift

7-Hydroxy-6-methoxy-1-tetralone (83 mg, 0.43 mmol) was subjected to reaction with O-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)hydroxylamine hydrochloride (96 mg, 0.48 mmol) in ethanol (2 mL) and pyridine (0.2 mL, 2.58 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 the title compound as off-white crystals (13 mg, 9%), m.p. 138° C. (with decomposition), Rf 0.4.

Quelle