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OH
HO

CH3
NH

OH
HO

NH2
HO

HO

HO

H
N

NH2

H
N
N
CH3

NH2

NH2

CH3

Et2N

CH3
O
N

NH2

CH3

NH2

CH2CH2OH
S

Cl

( 1)

CH3

R1O
O
C
OCH3
O

C
O

N CH3

R2O
R1 = R2 = H

R1 = H; R2 = CH 3
R1 = R2 = Ac

O
Ph

O C

Me

Ph

CH2CH3
O C

N
Me

Me

Ph

1.008 A
H N
107.3 H

1.474 A
CH3 N H
C6H5
113 H 105.9

Ph

CH3

C6H5

CH3
H

CH3

Cl

CH3

CH3

H
Ph
CH3

H3C

C6H5

C6 H5 N

C6H5

CH3
Ph

Bn

Ph

CH3
Bn
N

pKa

pKa

NH3

9.24

CH3NH2

10.62

H2NCH2CH2NH2

9.92

(CH3)2NH

10.73

(CH3)3N

9.80

NH

11.31

C5H5N ()

5.23

NH

11.12

.NH
+

CH3

4.44

OCH3
F
Cl
NO2-

4.52
3.20
2.65
0.26

4.72
4.23
3.57
3.52
2.47

5.10
5.34
4.65
3.98
1.02

[(CH3)2CH]2NH + -C4H9Li
pKa -40

[(CH3)2CH]2NLi + C4H10
Li
N

[(CH3)3Si]2NLi

pKa -50


RBr + NH3
RNH3+Br-

+ NH3

RNH2 + RBr
R2NH2+Br- + NH3
R2NH + RBr
R3NH+Br- + NH3
R3N + RBr

+ RNH3 Br

RNH2 +

+ NH4 Br

R2NH2+BrR2NH + NH4+BrR3NH+BrR3N + NH4+BrR4N+Br-

CH3(CH2)6Br + NH3
3M
1M

C2H5OH
o

25 C

CH3(CH2)5CH2NH2 +
45 %

+ [CH3(CH2)5CH2]2NH + [CH3(CH2)5CH2]3N
43 %

1%


O
NK + RX

80-100 C

O
NR + NH2NH2*H2O
O

NR + KX

NH
NH

C2H5OH
O

+ RNH2

O
CO2Et

NK + Br
CO2Et

CO2Et

80 C

CO2Et
O
1) EtONa / EtOH
2) BnBr
O

NH2
OH

Bn
O

64 %

H+ ,t
H2O

N
O

CO2Et
Bn
CO2Et

CH3CH2CH2CH2CN

CN
CH3

LiAlH4

LiAlH4

CH3CH2CH2CH2CH2NH2
91 %
CH2NH2
88 %
CH3

C6H5CH2CN + H2

Ni
140 C

C6H5CH2CH2NH2
+ 70 %
C6H5CH2CH2NHCH2CH2C6H5

RCN + H2

20 %

RCH=NH + RCH2NH2

RCH2NH2
NC(CH2)8CN + H2

RCH=NCH2R + NH3

RCH2NHCH2R
100 .,125 C

H2N(CH2)10NH2
80 %


CONMe2

CH3O
CH3O

LiAlH4

CH2N(CH3)2

, 36 C

88 %

CH3O
O
CH2CNH2

LiAlH4
, 36 C

CH3O

CH2CH2NH2

CH3O

CH3O
NH2
O

B2H6
, 65 C

40 %

NH2
79 %

Cl
+ NaN3

N
C2H5OH

86 %

LiAlH4
C6H5CH2NH2
89 %
Br

NaN3, 30 oC
18 - - 6
CH3CN

N3

LiAlH4

NH2
54 %

+ NH3

-H2O

+ NH3

O + NH3

H2/Ni

-H2O

Ph

H
NH

-H2O

H
1

NH

PhCHO

H2/Ni

90 .,70 oC

NH

R2

NH2

C6H5CH2NH2
89 %

NaBH3CN

NH2
61 %

O + NH(CH3)2 + NaBH3CN

pH 2 - 3
C2H5OH

N(CH3)2
85 %


O
NH + H2C O

+
H

120 C

NCH3 + CO2

OH
100 C

+ NH2CHO

HCOOH, 9
66 %

O
R2NH + CH2O

R2NCH2OH

NH2

R2NCH2OH2

O
R2NCH3 + CO2

R2N=CH2 + H2O

R2N=CH2 H C
O

NOH

1) LiAlH4,
2) H3O

NH2
80 %

NOH

1)NaBH3CN, CH3OH
2) CH3COOH
81 %

NH2

-
CH3

CH3
NO2

NH2

Fe + HCl
C2H5OH

74 %

NO2

NH2

NO2

NH2
SnCl2
HCl

57 %

CHO

CHO
NO2

NH2
NaSH
CH3OH

NO2

79 - 85 %

NH2


O
NH2

COCl
C6H5

CH3(CH2)16COOH

NH2

NaOH,Cl2
H2O, 0-20 C

NH2

1) NaN3; t
2) H2O

HN3; 40 C
C6H6; H2SO4

C6H5

CH3(CH2)16NH2
96 %


Bu3N + BuBr

60 C

Et3N + C6H5CH2Cl
Ac2O + C6H5NH2

C6H13CHO + C6H5NH2

O + NH

Bu4N Br 95 %

60 C

C6H5CH2 NEt3 Cl
87 %

CH3CONHC6H5
98 %

0-20 C
CH3COOH

C6H13CH=NC6H5 + H2O

C2H5OH

82 %

n-CH3C6H4SO3H
o

,110 C

N
75 %


O
ArS-NHR

ArSO2Cl + RNH2

O
O
ArS-NR2

ArSO2Cl + R2NH

C6H5SO2Cl + RNH2

NaOH
H2O

O
C6H5S-N
O

H
R

O
C6H5S-NR Na
O


OCH3

N
n-NH2C6H4SO2NH

n-NH2C6H4SO2NH

OCH3

n-NH2C6H4SO2NH

N
S

C2 H5

OH
N

N
NH2

CH2

NH

C NH CH-COOH
CH2-CH2-COOH

n-

B9

4-
H

6.9 A

6.7 A

H O

2.3 A

O S O
NH2

2.4 A


(CH3)2NH + HCl + NaNO2

BuNH2 + HNO2

0-5 C
Bu
H2O

0-5 C
H2O

(CH3)2N-N=O 88 %
N-

+H+

-H2O

N N

O
BuCl

BuOH

5%

25%

10%

26%

0-5 C
Ar-N
ArNH2 + NaNO2 + 2HX
H2O

OH 13 %

Cl 3%

N X + NaX + 2H2O

RNH2 + NaOCl

R2NH + NaOCl

0-5 C
H2O
0-5 C
H2O

RNCl2

R2NCl


O2 N

NH2

CF3CO3H

O2N

CH2Cl2

NO2

50 C

NO2

NO2
88 %

O2 N

NH2

CF3CO3H

O 2N

CH2Cl2

NO2
86 %

50 C

H3 C

NH2

Ph
NH2

H2SO5

CH3CO3H
H2 O

N=O 73 %

CH3

Ph

Ph
NO

NOH

NH + H2O2

(C2H5)3N + H2O2

HCOOCH3

30 % H2O2
0-20 C

CH3

N-OH

78 %

95 %

(C2H5)3N+ OCH3

CH3
120 - 150 C

+ (CH3)3NOH

N+(CH3)2
O64 %

36 %

-

NHAc

HNO3
H2SO4

O2N

NHAc +

90 %

NHAc

90 %-

. HNO3

O2N

NO2

NHAc +
77 %

NH3 HSO4

NHAc

NHAc
23 % NO2

NH3

SO3

Br

NH2

NH2

H2O

Br2 +

Br

40 C
Br

COOH

75 %

COOH
COOH

COOH
NH2 + Cl2

H2O
40 C

Cl

NH2

69 -78 %

Cl

NH2

Br

(CH3CO)2O

NHCOCH3

NHCOCH3

H3O
-

Br

Br2
CH3COOH
50 C
NH2

1)POCl3
(CH3)2N
+HCN(CH3)2
2)H2O
O

(CH3)2N

CHO
80 - 85 %

NR2

NaNO2+HCl
0-5 C, H2O

N
O

NR2

80 - 90 %