For example nitrobenzene is obtained by nitration of benzene.

because nitro group is ring deactivating group, nitration of nitro benzene is more difficult than benzene.

Well a standard nitration with mixed acids at elevated temperatures.

One could just follow the nitration of its brother, acetylsalicylicacid (ASA) as in the same way TriNitroPhenol (TNP) is made.

yes because amine forming salt with acid and it will be meta active

Howard William Post has written:

'The nitration of substituted anilines ..' -- subject(s): Aniline, Nitration

'The chemistry of the aliphatic orthoesters' -- subject(s): Esters