反应详情

A solution of 31.5 parts of (4-amino-3-nitrophenyl)phenylmethanone, 15.2 parts of 1,2-propanediol and 5 parts of 4-methylbenzenesulfonic acid in 40 parts of butanol and 450 parts of methylbenzene is stirred and refluxed for 17 hours. The reaction mixture is cooled and 90 parts of ammonium hydroxide are added (to remove the 4-methylbenzenesulfonic acid). The organic phase is separated, washed with water, dried, filtered and evaporated. The residue is crystallized from methylbenzene. The product is filtered off (the filtrate is set aside), yielding a first fraction of 13.8 parts of 4-(4-methyl-2-phenyl-1,3-dioxolan-2-yl)-2-nitrobenzenamine; mp. 155.2° C. The filtrate, which was set aside, is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane, methanol and hexane (88:2:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding a second fraction of 3.6 parts of 4-(4-methyl-2-phenyl-1,3-dioxolan-2-yl)-2-nitrobenzenamine.

1. temperaturerefluxed for 17 hours
2. temperatureThe reaction mixture is cooled
3. customto remove the 4-methylbenzenesulfonic acid)
4. customThe organic phase is separated
5. washwashed with water
6. customdried
7. filtrationfiltered
8. customevaporated
9. customThe residue is crystallized from methylbenzene
10. filtrationThe product is filtered off (the filtrate