[pgsj77]

Is it possible for the nitrogen on an aromatic nitro group to be attacked by a nucleophile like methanol in acidic conditions? Or is it more likely that, in the same conditions, the nitro group will attack a very electrophilic substrate if around the aryl ring there is a electron donating group ortho to the nitro group.

[pgk]

Try to draw the mechanisms in both cases. You will get the answer.

[pgk]

A good example is the Von-Richter rearrangement which describes the conversion of para-chloronitrobenzene into meta chlorobenzoic acid by the action of cyanide ion (cyanide salt).
p-Cl-Φ-ΝΟ2  +  KCN (+ H2O) →  →   m-Φ-COOH
Try to draw the mechanism.