$C{{H}_{3}}-N{{H}_{2}}+2HONO\,\to C{{H}_{3}}-ONO+{{N}_{2}}+2{{H}_{2}}O$
while dimethylamine and trimethyl amine form insoluble compound with hinsberg reagent and $KOH$.
${{R}_{2}}NH\,+\,{{C}_{6}}{{H}_{5}}S{{O}_{2}}Cl\,\xrightarrow{O{{H}^{-}}}$ ${{C}_{6}}{{H}_{5}}S{{O}_{2}}N{{R}_{2}}$
${{R}_{3}}N\,+\,{{C}_{6}}{{H}_{5}}S{{O}_{2}}Cl\,\xrightarrow{O{{H}^{-}}}\underset{insoluble}{\mathop{{{R}_{3}}N}}\,$
Azo dyes are not formed by secondary amines.
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Reason : $sp$ hybridised carbon atoms of acetylene are considerably electronegative.
