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Est. 1984
ISSN: 0970-020 X
CODEN: OJCHEG
2011, Vol. 27, No. (3):
Pg. 991-996
INTRODUCTION
Reduction of nitro compounds is one of
the important methods for the preparation of aryl
amines. Nitro compounds have traditionally been
reduced by high-pressure hydrogenation1. The
application of NaBH4 as a mild reducing agent has
brought about fundamental changes in the reduction
of functional groups in modern organic synthesis. It
is known that solely sodium borohydride does not
reduce nitro compounds under ordinary conditions
2
. However, the reducing power of this reagent or
its polymeric analogue i.e., borohydride exchange
resin (BER) undergoes a drastic change toward
reduction of nitro groups by the combination with
transition metal halides or salts such as NaBH4/
CoCl2 3, NaBH4/FeCl2 4, NaBH4/CuSO4 5, NaBH4/
992
Scheme 1.
We applied the optimal conditions for the
reduction of a variety of nitro compounds to their
corresponding amines. As shown in Table 4. The
product amines were obtained in high to excellent
yields within 2060 minutes. The chemoselective
reduction of nitro group in the presence of carboxylic
acid was proven with the reduction of 2-nitrobenzoic
acid to anthranilic acid in 94% yield (table 4, entry
4). Our attempts to reduce C=O over nitro group in
2-nitrobenzaldehyde and 32 -nitroacetophenone
were unsatisfactor y and under the different
993
Molar ratio
Subs/NaBH4/NiCl2.6H2O
Condition
Time/h
Yield%a
1:4:0.2
1:4:0.2
1:8:0.2
1:8:0.5
RT
Reflux
Reflux
Reflux
1
1
1
1
5
25
40
50
1
2
3
4
a
Molar ratio
Subs/NaBH4/Ni(OAc)2.4H2O
Condition
Time/h
Yield%a
1:4:0.2
1:4:0.2
1:8:0.2
1:8:0.5
RT
Reflux
Reflux
Reflux
1
1
1
1
10
35
45
60
1
2
3
4
a
1
2
3
4
5
6
7
8
a
Molar ratio
Subs/NaBH4/Ni(OAc)2.4H2O
1:4:0.2
1:4:0.2
1:4:0.2
1:4:0.2
1:4:0.2
1:4:0.2
1:4:0.4
1:4:0.2
Solvent
THF
THF
CH3CN
CH3CN
CH3CN/H2O(3:0.5ml)
CH3CN/H2O(3:0.3ml)
CH3CN/H2O(3:0.3ml)
CH3CN/H2O(3:0.15ml)
Condition
Time/h
Yield%a
RT
Reflux
RT
Reflux
RT
RT
RT
RT
60
60
60
180
60
20
60
60
0
15
10
50
60
92
80
70
994
995
REFERENCES
1.
2.
3.
4.
5.
6.
996
7.
8.
9.
10.
11.