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How to convert benzamide to benzylamine?
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Nicole Williams
How to convert benzamide to benzylamine?
The more reactive $\ce{LiAlH4}$ is required for the reduction of the amide to the corresponding amine (source). The carbonyl carbon of an amide is less electrophilic compared to a ketone, because electron density is donated by the amide nitrogen via resonance.
Bromine and hydroxide react with an carboxylic acid amide to yield an amine with one fewer carbon atom (Hofmann degradation). $\ce{Br2}$ and $\ce{KOH}$ react to form $\ce{KOBr}$ in situ, which transforms the amide into an intermediate isocyanate ($\ce{R-N=C=O}$). Hydrolysis of the isocyanate yields a carbamic acid $\ce{R-NH-COOH}$, which decomposes to the amine $\ce{R-NH2}$ and $\ce{CO2}$. As described in this paper, the reaction of $\ce{PCl5}$ with carboxylic acid amides produces amidochlorides $\ce{RCCl2NH2}$ as intermediates, which break down to the corresponding nitrile $\ce{RC#N}$ and $\ce{HCl}$.
The more reactive $\ce{LiAlH4}$ is required for the reduction of the amide to the corresponding amine (source). The carbonyl carbon of an amide is less electrophilic compared to a ketone, because electron density is donated by the amide nitrogen via resonance.
Bromine and hydroxide react with an carboxylic acid amide to yield an amine with one fewer carbon atom (Hofmann degradation). $\ce{Br2}$ and $\ce{KOH}$ react to form $\ce{KOBr}$ in situ, which transforms the amide into an intermediate isocyanate ($\ce{R-N=C=O}$). Hydrolysis of the isocyanate yields a carbamic acid $\ce{R-NH-COOH}$, which decomposes to the amine $\ce{R-NH2}$ and $\ce{CO2}$. As described in this paper, the reaction of $\ce{PCl5}$ with carboxylic acid amides produces amidochlorides $\ce{RCCl2NH2}$ as intermediates, which break down to the corresponding nitrile $\ce{RC#N}$ and $\ce{HCl}$.
The more reactive $\ce{LiAlH4}$ is required for the reduction of the amide to the corresponding amine (source). The carbonyl carbon of an amide is less electrophilic compared to a ketone, because electron density is donated by the amide nitrogen via resonance.
Bromine and hydroxide react with an carboxylic acid amide to yield an amine with one fewer carbon atom (Hofmann degradation). $\ce{Br2}$ and $\ce{KOH}$ react to form $\ce{KOBr}$ in situ, which transforms the amide into an intermediate isocyanate ($\ce{R-N=C=O}$). Hydrolysis of the isocyanate yields a carbamic acid $\ce{R-NH-COOH}$, which decomposes to the amine $\ce{R-NH2}$ and $\ce{CO2}$. As described in this paper, the reaction of $\ce{PCl5}$ with carboxylic acid amides produces amidochlorides $\ce{RCCl2NH2}$ as intermediates, which break down to the corresponding nitrile $\ce{RC#N}$ and $\ce{HCl}$.
The more reactive $\ce{LiAlH4}$ is required for the reduction of the amide to the corresponding amine (source). The carbonyl carbon of an amide is less electrophilic compared to a ketone, because electron density is donated by the amide nitrogen via resonance.
Bromine and hydroxide react with an carboxylic acid amide to yield an amine with one fewer carbon atom (Hofmann degradation). $\ce{Br2}$ and $\ce{KOH}$ react to form $\ce{KOBr}$ in situ, which transforms the amide into an intermediate isocyanate ($\ce{R-N=C=O}$). Hydrolysis of the isocyanate yields a carbamic acid $\ce{R-NH-COOH}$, which decomposes to the amine $\ce{R-NH2}$ and $\ce{CO2}$. As described in this paper, the reaction of $\ce{PCl5}$ with carboxylic acid amides produces amidochlorides $\ce{RCCl2NH2}$ as intermediates, which break down to the corresponding nitrile $\ce{RC#N}$ and $\ce{HCl}$.
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