Meltonium
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4-Chloroaniline
4-Chloroaniline is an important precursor to many pharmaceuticals and dyes as well. Industrially, it is produced by first nitrating chlorobenzene and
then hydrogenating the nitro group to form the amine.
Would an additional way to produce 4-chloroaniline be by adding liquid ammonia to liquid p-dichlorobenzene?
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Metacelsus
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First of all, liquid ammonia would boil if you added it to liquid p-dichlorobenzene (and the p-dichlorobenzene would freeze).
The production of aniline by addition of chlorobenzene to a solution of sodium amide in liquid ammonia goes through a benzyne intermediate, so
p-dichlorobenzene would result in a mixture of isomers, if it didn't just react twice.
There is some precedent for nucleophilic substitution on p-dichlorobenzene; on treatment with sodium sulfide, it forms poly(p-phenylene sulfide).
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