Cyclohexylamine → Ethyl 4-(cyclohexylamino)-3-nitrobenzoate

Participants

Reaction Steps

Ethyl 4-fluoro-3-nitrobenzoate (5.73 g, 0.0269 mol) was dissolved in 25 mL of DMF. While stirring under an atmosphere of nitrogen, cyclohexanamine in 5 mL of DMF (3.4 mL, 0.030 mol) and N,N-diisopropylethylamine (14 mL, 0.080 mol) were added simultaneously via two seperate syringes. The reaction mixture turned immediately into a deep yellow/orange gel and was diluted with another 5 mL of DMF. The reaction mixture was slightly exothermic and stirring was maintained until the reaction was complete as determined by LC/MS. The reaction mixture was then diluted with ethyl acetate and washed with 5% citric acid then brine. The organic phase was collected, dried over sodium sulfate and concentrated to a yellow oil which solidified under high vacuum to yield 8.47 g of the title compound.

Provenance & Evidence