Which proton is more acidic in this compound? I'm having trouble determining which of these protons is more acidic. I was thinking the solution had something to do with the double bond in the aromatic ring, but I'm still not sure.
You could start by drawing the resonance structure of the naphthalene ring, this gives a compound in which the conditions on the two nitrogen atoms are interchanged, thus both nitrogen atoms are equivalent. As $\ce{N-H}$ bonded protons are more acidic than $\ce{C=C-H}$ protons and $\ce{N-C-H}$ protons, the answer must be the hydrogen atom bonded to the nitrogen atom, as both nitrogen atoms are equivalent, either of the hydrogen atoms is a valid answer (as they are equivalent).