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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 HCl N HCl N
Na+ O - O O O ≡O + H2O
+N
..
.. HO H2O+
..
..
.. ..
1
.. N HCl .. N HCl
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
..
HCl Cl⊖
nitrosoamine
5 6
.. .. ..
N =NOH2 -H O
.. ..
N =N..
OH 2
..
HCl
n-hydroxyazo
compound
⊖
Cl
N≡N
7
phenyldiazonium chloride
.. ⊖ ..
O OH
..
..
..
Na I I
.. N HCl .. N HCl
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