Module 4 - Naphthalene derivatives - Naphthyl amines- 1-Naphthyl amines - 2- Naphthyl amines - Preparation - Bucherer reaction- Reactions of naphthylamines

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2. Preparation of naphthyl amines
There are two isomeric naphthyl amines.
i)  -Naphthyl amine is manufactured by the reduction of -nitro naphthalene with
iron and HCl.
ii) But -naphthylamine is manufactured from -naphthol. This reaction is known as
Bucherer reaction.
iii) -Naphthylamine is also prepared by heating -naphthol with NH3 and ZnCl2 at
250oC.

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Reactions of naphthylamines
i) Electrophilic substitution reactions: They undergo halogenation, nitration,
sulphonation etc. However, to avoid formation of polysubstituted derivatives amino
group must be protected through acylation.
In case of -naphthylamine the incoming substituent generally enters at 4-position
while in -naphthylamine it enters at 1-position.
ii) Reduction : They are reduced by sodium and isoamyl alcohol. -Naphthylamine
forming (5,6,7,8-tetrahydro-naphthylaine), while -naphthylamine gives 1,2,3,4-
tetrahydro-2-naphthylaine.
iii) Oxidation: They are highly susceptible to oxidation and reduce ammoniacal silver
nitrate. Oxidation with acidified KMnO4 gives phthalic acid.

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Prepared by
Dr. A. Syed Mohamed
HoD and Senior Assistant Professor, Research Dept. of Chemistry
Sadakathullah Appa College (Autonomous)
Tirunelveli, Tamilnadu, India. asm2032@gmail.com
The author ackowledges Prof. H. Kassali Rahmathullah, Dr. T. Syed Ismail, Dr. M.
Kamalutheen, Former Professor, Dept. of Chemistry, Sadakathullah Appa College for their
valuable contribution.