2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Benzenesulfonyl-naphthalene-1-carbonitrile

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Reaction Steps

A mixture of 0.89 g (3 mmoles) 6-benzenesulfonyl-3,4-dihydro-naphthalene-1-carbonitrile and 0.68 g (3 mmoles) DDQ in 15 mL dioxane was heated under reflux for 18 hours. Another 0.25 g (0.12 mmole) DDQ was added and the reaction mixture was heated under reflux for another 20 hours. The mixture was filtered and the collected solids were washed with diethyl ether. The filtrate was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and washed with 5% sodium hydroxide and half-saturated aqueous sodium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to column chromatography over silica gel 230-400 mesh eluting with chloroform:hexane:ethyl acetate (50:49:1), then with 50:48:2 and finally with 50:46:4. The title compound was obtained as a white solid, 0.266 gram (30%). NMR (CDCl3) ppm δ: 8.67 (d, 1H, J=1.8 Hz), 8.34 (d, 1H, J=8.8 Hz), 8.24 (d, 1H, J=8.41 Hz), 8.04 (m, 4H), 7.69 (dd, 1H, J=4.25 Hz, J=11.5 Hz), 7.56 (m 3H).

Provenance & Evidence