Cyclohexene → 4-Chloro-2-methyl-3-nitroaniline

Participants

Reaction Steps

A mixture of 3-chloro-2,6-dinitrotoluene (2.46 g, 9.5 mmol), cyclohexene (10 mL) and 10% palladium on charcoal (0.6 g) in ethanol (50 mL) was heated at reflux under an atmosphere of nitrogen for 2 h. After this time the reaction mixture was cooled to room temperature, filtered through celite and then evaporated under reduced pressure. The residue was dissolved in diethyl ether and filtered through a short silica column. Evaporation of the ether afforded the product as an orange solid. 1H NMR (400 MHz) (CDCl3) δ 7.15 (d, J=8.7 Hz, 1H); 6.72 (d, J=8.7 Hz, 1H); 3.80 (bs, 2H); 2.11 (s, 3H).

Provenance & Evidence