Both nitrogen atoms are attached to the ring by electrophilic aromatic substitution. In one of the steps, two products will be formed. The correct product must be isolated following that step or a succeeding step, but that isolation is not shown as one of the steps.

In each reaction box, place the best reagent and conditions from the list below. (A reagent may be used more than once.) NH2 2) 3) 4) NO2 5) 6) So3, H2SO4 HNO2, H2SO4 CH3COOH acetyl chloride, pyridine NANO3 HNO3, H2SO4 H30*, H20, A Br2, A H2, Pd NaOH (room temp.) Br2, FeBr3