By a primary amine I mean a compound where the hydroxyl group of the corresponding alcohol is replaced with an amine group.
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For aliphatic compounds you can use alkylation $$\ce{R-OH + NH3 -> R-NH2 + H2O}$$ For aromatic compounds like phenol $$ \begin{matrix} \ce{C6H6O &\quad +& Zn& \ ->& C_6 H_6\\ Phenol& & (dust\ form)& \ & Benzene&} \end{matrix} $$ Zinc dust reduces the OH group in phenol $$\begin{matrix} \ce{C6H6& + &HNO3_{(aq)}& ->& C6H5NO2 + &H_2 O&\\ Benzene& & (high\ concentration)&& Nitrobenzene& water& } \end{matrix}$$ Nitration $$\begin{matrix}
\ce{C6H5NO2& +& Sn& +& \qquad HCl_{(aq)} ->& C6H5NH2&\\
Nitrobenzene& & Tin& &Hydrochloric & Aniline&\\
&&&&acid}
\end{matrix}$$
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In addition to the method provided by t3st you could also try the following for $$\begin{matrix} \ce{Ph-OH& +& Zn& ->& C6H6 \\ Phenol& & Zinc& & Benzene&} \end{matrix}$$ (Just like the first step of t3st 's answer. Then you could do Electrophilic halogenation of benzene using $\small\ce{AlCl3\ or\ FeBr3}$ as catalyst. $$\begin{matrix} \ce{C6H6& ->[\ce{Cl2/AlCl3}]& Ph-Cl\\ Benzene& & Aryl\ halide&} \end{matrix}$$ Finally you could react aryl-halide with soda-amide($\small\ce{NaNH2}$) to substitute $\ce{Cl}$ with $\ce{NH2}$[citation needed] $$\begin{matrix} \ce{Ph-Cl& ->[\ce{NaNH2}]& Ph-NH2&\\ Aryl halide& & Aniline&} \end{matrix}$$ |
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