
${C_6}{H_5}N{H_2}\mathop {\xrightarrow{{NaN{O_2}/HCl}}}\limits_{0 - 5\,^o C} X\mathop {\xrightarrow{{HN{O_2}}}}\limits_{C{H_2}O} Y + {N_2} + HCl$
$X$ and $Y$ are respectively


Isomer $(P) \Rightarrow$ Can be prepared by Gabriel phthalimide synthesis
Isomer $(Q) \Rightarrow$ Reacts with Hinsberg's reagent to give solid insoluble in $NaOH$
Isomer (R) $\Rightarrow$ Reacts with $HONO$ followed by $\beta$-naphthol in $NaOH$ to give red dye.
Isomers $( P ),( Q )$ and $( R )$ respectively are
$C{{H}_{3}}OH\xrightarrow{HI}C{{H}_{3}}I\xrightarrow{KCN}$
$C{{H}_{3}}CN\xrightarrow{\text{reduction}}X\xrightarrow{HN{{O}_{3}}}Y$