p-Fluoronitrobenzene → 4-nitro-N-prop-2-ynylaniline

Participants

Reaction Steps

A mixture of 26.6 g (189 mmol) of 4-fluoronitrobenzene, 20.8 g (377 mmol) of propargylamine, 11 g (189 mmol) of potassium fluoride, and 26 g (188 mmol) of potassium carbonate in 600 ml of dimethylsulfoxide is stirred at room temperature under a nitrogen atmosphere for twenty hours. The reaction mixture is poured into 1.5 l of water and stirred at room temperature for two hours. The yellow solid is filtered, rinsed with water, and then isopropyl alcohol. The product is dried in vacuo at 50° C. for two days to give 16.27 g (49%) 4-nitro-N-2-propynylbenzenamine; mp 150°-153° C.

Provenance & Evidence