N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide → N-(2-fluoro-5-aminophenyl)-3,4,5,6-tetrahydrophthalimide

Participants

Reaction Steps

Wet Raney Nickel (0.9 g) is added to a solution of N-(2-fluoro-5-nitrophenyl)-1-cyclohexene-1,2-dicarboximide (1.0 g, 3.4 mmol) in a 4:1 ethylene glycol dimethyl ether/ethanol solution. The reaction mixture is hydrogenated over 45 psi of hydrogen until the reaction mixture takes up 9 psi. The reaction mixture is filtered through diatomaceous earth and concentrated in vacuo to obtain a yellow residue. Chromatography of the residue gives the title product as a yellow-orange solid (0.84 g, mp 134°-136° C.) which is identified by 1H and 13C NMR spectral analyses.

Provenance & Evidence