2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 9-[(3-Chlorophenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole

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Reaction Steps

A solution of the 9-[(3-chlorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one (480.5 mg, 1.31 mM) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (325.7 mg, 1.43 mM) in 50 mL of toluene was stirred between 70-80° C. for 3 hours. The mixture was purified directly by column chromatography on silica gel (elution with methylene chloride) to afford 172.6 mg (36%) of the 9-[(3-chlorophenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole as a yellow foam. 1H NMR (CDCl3) δ10.4 (s, 1H), 8.05 (d, 1H, J=8 Hz), 7.6 (d, 1H, J=8 Hz), 7.4 (m, 2H), 7.3-7.1 (m, 3H), 6.9-6.7 (m, 3H), 5.55 (s, 2H), and 4.15 (s, 3H). IR (CDCl3, cm−1) 3200 (br), 1684, 1598, 1442, 1428, 1331, 1285, and 1267. MS (ES) m/e 364, 366, 368.

Provenance & Evidence