Ethylene Glycol → 4-(2-(4-Fluorophenyl)-1,3-dioxolan-2-yl)-2-nitroaniline

Participants

Reaction Steps

A mixture of 26 parts of (4-amino-3-nitrophenyl)(4-fluorophenyl)methanone, 12 parts of 1,2-ethanediol, 10 parts of 4-methylbenzenesulfonic acid, 32 parts of butanol and 360 parts of benzene is stirred and refluxed for 96 hours with water-separator. Another 5 parts of 4-methylbenzenesulfonic acid are added and stirring at reflux is continued for 72 hours. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is purified twice by column-chromatography over silica gel using first a mixture of trichloromethane and 2% of methanol and then trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding 10.1 parts (33.2%) of 4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-2-nitrobenzenamine; mp. 105° C.

Provenance & Evidence