The Synthetic Routes of 4-Formyl-N-(1-methylethyl)benzamide

4-Formyl-N-(1-methylethyl)benzamide is an important intermediate in the synthesis of various pharmaceuticals, agricultural chemicals, and other fine chemicals.
The synthesis of this compound has been extensively studied in the chemical literature, and several synthetic routes have been reported.

One of the most common synthetic routes for 4-formyl-N-(1-methylethyl)benzamide involves the reaction of 4-nitrobenzaldehyde with 1-methylethylamine in the presence of a strong acid catalyst, such as sulfuric acid.
This reaction is exothermic and requires careful handling.
The reaction mixture is then treated with a base, such as sodium hydroxide, to liberate the amide.
This route is shown below:

                H2O
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                H+
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             +---> 4-nitrobenzaldehyde (nitrobenzene)
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            H2N-CH2-CH2-NH3 +  H+      H2O
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            4-Formyl-N-(1-methylethyl)benzamide

Alternatively, the synthesis of 4-formyl-N-(1-methylethyl)benzamide can be achieved through the reaction of 4-bromobenzaldehyde with 1-methylethylamine in the presence of a base, such as sodium hydroxide.
The reaction mixture is then treated with a mineral acid, such as hydrochloric acid, to liberate the amide.
This route is also shown below:

                H2O
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                H+
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             H2N-CH2-CH2-NH2 +  H+      H2O
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            4-Formyl-N-(1-methylethyl)benzamide

Another synthetic route for 4-formyl-N-(1-methylethyl)benzamide involves the reaction of 4-chlorobenzaldehyde with 1-methylethylamine in the presence of a Lewis acid catalyst, such as boron trifluoride etherate.
The reaction mixture is then treated with a base, such as sodium hydroxide, to liberate the amide.
This route is shown below:

                H2O
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                H+
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            H2N-CH2-CH2-NH2 +  H+      H2O
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            4-Formyl-N-(1-methylethyl)benzamide