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

Participants

Reaction Steps

A solution of 9-[(cyclopentyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one (730 mg, 2.24 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (560 mg, 2.47 mmol) in 20 mL of toluene was heated at 80° C. for 3 hours. The mixture was purified directly by column chromatography on silica gel (elution with CH2Cl2) to afford 140 mg (0.433 mmol; 19%) of 9-[(cyclopentyl)methyl]-4-hydroxy-5-carbomethoxy carbazole as a yellow oil which slowly solidified. MS (ES) m/e 324 (M+1), 322 (M−1).

Provenance & Evidence