Pyridine → (E)-5,6-dimethoxy-N-[(4-nitrophenyl)methoxy]-2,3-dihydroinden-1-imine

Participants

Reaction Steps

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.

Provenance & Evidence