[prozen]

http://imgur.com/a/fkvpk

Just thinking about the above reaction. One can make the product by using the starting material shown and the fluoroaniline.

In terms of the mechanism, does the aniline attack the nitrated imidazole nitrogen, displace the nitro group which picks up a proton to form HNO2 and subsequently decomposes to NO2?

[AWK]

ANRORC mechanism