Cyclohexanone → 3-Methoxy-9H-carbazole

Participants

Reaction Steps

Bis-1,3(N-3'-methoxycarbazolyl)propane. Reaction of p-methoxyphenylhydrazine hydrochloride with cyclohexanone (exothermic) was carried out as for the methyl substituted compound (See Liebigs Ann. der Chemie, 359, 52, 1908) in 82% yield, mp 105°-7.5° C. This compound was dehydrogenated with 10% palladium on charcoal in xylene, as above, to give 74% of 3-methoxycarbazole, recrystallized from benzene/heptane, mp 148.5°-9.5° C (lit. mp 150.5°-1.0° C).

Provenance & Evidence