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N

NH2 Cl- +
N

diazotization
HCl + NaNO2
aniline phenyldiazonium
chloride
N N
Cl- +
N N
OH OH
coupling
+
NaOH
phenyldiazonium β-naphthol 1-phenylazo-2-
chloride naphthol
N
NH2 Cl- +
N

diazotization
HCl + NaNO2
aniline phenyldiazonium
chloride
N
Cl- +
N
OH
coupling N
+ N
NaOH OH
phenyldiazonium β-naphthol
chloride

1-phenylazo-2-
naphthol
.. N HCl N HCl N
Na+ O - O O O ≡O + H2O
+N
..

.. HO H2O+

..
..

.. ..
1

.. N HCl .. N HCl
Na+ O O
..

..
O - ..
.. HO..
..

..

-H2O 2
N +N ≡O

..
H2O+ O
..

..
..
H H H H
1 .. 2
N N+  N=O

..
.. 
NaNO2
..
+N ≡O

3 ..
H H 4
.. .. ..
..
N N=O N+=N..
OH
..

HCl  Cl⊖
nitrosoamine

5 6
.. .. .. 
N =NOH2 -H O
.. ..
N =N..
OH 2
..
HCl
n-hydroxyazo
compound

Cl 
N≡N
7
phenyldiazonium chloride
.. ⊖ ..
O OH

..
..
..

Na I I
.. N HCl .. N HCl
O O
..

..

.. O ⊖
..
..

..
.. ..

-H2O 2
N +N ≡O

..
H2O+ O
..

..
..
.. ⊖
O--H  ⊖ O

..
..
Na OH

.. .. N≡N
O
..


N
N
O

N
1-phenylazo-2-
N
naphthol
OH

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