Organic Reactions Volume 4 - Sciencemadness Dot Org

Amine, Nitro, Nitroso,
or Azo Compound Used
C6H5NO
C6H5NO2
0-CH3C6H4NH2
P-CH3C6H4NH2
^-CH3C6H4NO2
P-CH3C6H4NH2
P-CH3C6H4NO2
2,4,6-(CHs)3C6H2NH2
2,4,6-(CH3)3C6H2NH2
2,4,6-(CH3)3C6H2N02
P-ClC6H4NO2
P-HOC6H4NH2
P-HOC6H4NO2
P-HOC6H4NH2
P-HOC6H4NH2
P-HOC6H4NO2
P-HOC6H4NO2
P-HOC6H4NO
^HOC6H4NH2
TABLE X—Continued
PREPARATION OF SECONDARY AMINES
F. From Primary Aromatic Amines, Nitro, Nitroso, m • Azo Compounds and Aldehydes—Continued
Carbonyl Compound
C6H5CHO
C6H5CHO
CH3CHO
CH3CHO
CH3(CH2)2CHG
CH3(CH2)2CHO
CH3(CH2)5CHO
(CH3)2CHCHO
(CHa)2CHCH2CHO
(CH3)2CHCH2CHO
CH3(CH2)2CHO
CH3CHO
CH3(CH2)2CHO
CH3(CH2)2CHO
(CH3)2CHCHO
(CHs)2CHCHO
(CHs)2CHCHO
(CHs)2CHCHO
CH3(CHs)3CHO
Reducing Agent
H2 + Ni
H2 + Ni
Zn -f H2SO3
H2 + Ni
H2 + Ni
H2 + Ni
H2 + Ni
Zn + HCl
Zn + HCl
Zn -f HCl
H2 + Ni
Al + NaOH
H2 -f Ni
Al + NaOH
H2 + Ni
H2 + Ni
Zn + NaOH
H2+Pt
Al + NaOH
Products Isolated
C6H5NHCH2C6H5
C6H5NH2
C6H5NHCH2C6H5
0-CH3C6H4NHCH2CH3
P-CH3C6H4NHCH2CH3
P-CH3C6H4NH(CH2)SCH3
p-CH3C6H4N[(CH2)3CH3I2
P-CH3C6H4NH(CH2)SCH3
p-CH3C6H4N[(CH2)3CH3]2
p-CHgCgH^HfCH^eCHs
p-CH3C6H4N[(CH2)6CH3]2
2,4,6-(CHs)3C6H2NHCH2CH(CHg)2
2,4,6-(CH3)3C6H2NH(CH2)2CH(CHs)2
2,4,6-(CH3)3C6H2NH(CH2)2CH(CH3)2
P-ClC6H4NH2
p-ClCeH^H^H^CHs
C6H5NH (CH2) 3CH2
P-HOC6H4NHCH2CH3
P-HOC6H4NH(CH2)SCH3
P-HOC6H4Nt(CH2)SCH3I2
P-HOC6H4NH(CH2)SCH3
P-HOC6H4NHCH2CH(CHS)2
P-HOC6H4NHCH2CH(CHS)2
P-HOC6H4NHCH2CH(CHS)2
P-HOC6H4NHCH2CH(CHS)2
p-HOC6H4NH(CH2)4CH3
Yield, %
47
33
80
50
85,40
53
58
19
35
34
91
94
61
—
—
—
56
39
—
28, 77, 90
82
—
—
—
Ref.*
47
43
35
36
43
36
33,43
42
42
42
33
37, 38
45
37,38
64
45
45
45
37, 38
to
to
Oi
O
O
>
O
>
O
t—i
O
Ul