Vanadium pentoxide as a catalyst for regioselective nitration of organic compounds under conventional and nonconventional conditions

Article abstract of DOI:10.1080/15533174.2013.790431

Vanadium pentoxide is used as an efficient catalyst for regioselective nitration of aromatic compounds under conventional and nonconventional conditions such as ultrasonically assisted (USAR) and microwave-assisted reactions (MWAR). The reactions underwent smoothly and afforded good yields of products with high regioselectivity. Observed longer reaction times (about 8 h) in V₂O₅ catalyzed reactions reduced to (0.5/30 min) under sonication and (90 s) in the case of MWAR. When ortho position is blocked, para derivatives are obtained as end products while ortho nitro products are obtained when para position is blocked.

Full text of DOI:10.1080/15533174.2013.790431

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44:921–926, 2014
Copyright ꢀ Taylor & Francis Group, LLC
C
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2013.790431
Vanadium Pentoxide as a Catalyst for Regioselective
Nitration of Organic Compounds under Conventional
and Nonconventional Conditions
N. Venkatesham, K. Rajendar Reddy, K. C. Rajanna, and P. Veerasomaiah
Department of Chemistry, Osmania University, Hyderabad, A.P., India
and Wilkinson[5] in this area of chemistry are highly notewor-
Vanadium pentoxide is used as an efficient catalyst for regios-
elective nitration of aromatic compounds under conventional and
nonconventional conditions such as ultrasonically assisted (USAR)
and microwave-assisted reactions (MWAR). The reactions under-
went smoothly and afforded good yields of products with high re-
gioselectivity. Observed longer reaction times (about 8 h) in V2O5
catalyzed reactions reduced to (0.5/30 min) under sonication and
(90 s) in the case of MWAR. When ortho position is blocked, para
derivatives are obtained as end products while ortho nitro products
are obtained when para position is blocked.
thy. Transition metal-catalyzed reactions are one of the most
powerful and direct approaches for the synthesis of organict
molecules.
Vanadium is a d-transition metal found in Group VA of
the Periodic Table. Vanadium’s ground state electron config-
uration is [Ar] 3d34s2. When transition elements ionize, they
lose their valence s electrons before losing their d electrons.
Vanadium has five valence electrons that can be lost. Vana-
dium exhibits four common oxidation states +5, +4, +3, and
+2 each of which can be distinguished by its color. Vana-
dium (V) oxide is commonly known as vanadium pentoxide
(V2O5) or vanadia. Because of its high oxidation state, it is
both an amphoteric oxide and an oxidizing agent, which catal-
yses several useful aerobic oxidation reactions, the largest scale
of which underpins the production of sulfuric acid from sul-
fur dioxide. It is used as an efficient catalyst for the aerobic
and nonaerobic oxidation of alcohols with good regioselectiv-
ity. Primary alcohols were converted to aldehydes and secondary
alcohols to ketones with a catalytic amount of V2O5 in toluene at
100◦C.
Keywords microwave irradiation, rate accelerations, regioselective
nitration, sonication, vanadium pentoxide
INTRODUCTION
The transition metals are the group of metals in the middle
section of the periodic table, which have one s, three p, and
five d orbitals that possess geometrical and energetic features
suitable for bonding with the ligands. The outermost incom-
pletely filled d orbitals facilitate them to accept and donate
electrons. By giving and taking electrons so easily, transition
metal catalysts speed up reactions. In view of this important
behavior of transition metals, there has been an upsurge since
the 1940s, in the area of catalysis research in general and tran-
sition metal catalysis complexes in particular. This also resulted
in a rapid development of newer process technologies relevant
to industrial scale reactions for the production of organic com-
pounds using transition metal complexes as catalysts.[1] The
demand for cheaper and more efficient processes in the indus-
try necessitated a major explosion of research in the area of
synthetic chemistry to develop new systems that can act as cat-
alysts.[2] The contributions of Ziegler and Natta,[3] Fischer[4],
Recently Clark and Rothenberg[6] have demonstrated
Vanadium-catalysed oxidative bromination by means of dilute
mineral acids, hydrogen peroxide, and alkali bromides. The de-
veloped methodology was effective for the bromination of acti-
vated and nonactivated (but not deactivated) aromatic substrates.
An option of using H2SO4, HNO3, HBr, HCl, and (to a lesser
extent) H3PO4 was also suggested as an option for recycling
industrial acid waste. In another method, Bhattacharjee et al.[7]
used vanadium (V) or molybdenum (VI), KBr, and hydrogen
peroxide in aqueous medium for electrophilic bromination of
organic compounds. Even though several methods are available
on the nitration of organic compounds,[8–10] vanadium pentoxide
has not been explored as a catalyst so far. As a part of our on-
going work on the exploration of transition metal-catalysed or-
ganic transformations under conventional and nonconventional
conditions,[11–13] we wish to present certain interesting results
using vanadium pentoxide as a catalyst for effective nitration
of organic compounds under conventional and nonconventional
conditions.
Received 6 February 2013; accepted 23 March 2013.
Address correspondence to K. C. Rajanna, Department of Chem-
istry, Osmania University, Hyderabad 500 007, A.P., India. E-mail:
kcrajannaou@yahoo.com
921

922
N. VENKATESHAM ET AL.
TABLE 1
EXPERIMENTAL DETAILS
Effect of solvent and V2O5 on nitration of phenol under
conventional conditions
Materials and Methods
Laboratory-grade reagents and substrates were procured
from Merck, SD fine chemicals, or Alfa Aesar. Doubly distilled
water (distilled over alkaline KMnO4 and acid dichromate in an
all glass apparatus) was used whenever required. HPLC-grade
solvents were used as such. Laboratory model microwave re-
actor (CEM-908010, bench mate model, 300 W equipped with
temperature, pressure, and microwave power control units) was
used for microwave-assisted reactions (MWAR) in this study.
S. No.
Solvent
V2O5 (mmol)
Time (hr)
Yield (%)
0.001
0.002
0.005
0.01
0.001
0.002
0.005
0.01
0.001
0.002
0.005
0.01
08
08
08
08
11
11
11
11
13
13
13
13
65
70
80
77
65
68
75
70
60
63
65
60
1
DCE
2
3
ACN
Typical Experimental Procedure for Nitration of Organic
Compounds under Conventional Conditions
In a typical experiment, phenol (0.094 mL, 1 mmol) and
V2O5 (9 mg, 0.005 mmol) were suspended in dichloroethane
(10 mL), followed by the addition of 69% HNO3 (0.063 mL,
1 mmol). The reaction mixture was stirred at room temperature
till the completion of reaction as indicated by TLC. The reaction
mixture was filtered off and washed with water; and the organic
layer was separated out dried over sodium sulphate and evapo-
rated under vacuum. The crude product was purified by column
chromatography using ethyl acetate: hexane (3:7) as eluent. IR,
NMR, and mass spectroscopic analysis of the product indicated
that phenol afforded p-nitrophenol as the major end product
with 85% yield (Exptal m.p 113◦C (lit. mp. 114◦C).
MeOH
RESULTS AND DISCUSSION
In order to optimize the reaction conditions, nitration re-
actions are performed in different solvent media using varied
amounts of V2O5 (0.001 to 0.01 mol/dm3) as catalyst. Table 1
shows reaction times and percentage (%) yield of nitration of
phenol under different reaction conditions. The reaction under-
went smoothly in DCE when 0.005 mmol of V2O5 was used
as a catalyst. Keeping this in view, 0.005 mol of V2O5 is used
throughout the study.
Typical Procedure for Ultrasonic-Assisted Nitration
(USNAR) of Organic Compounds
Methodology for USNR of organic compounds is by and
large similar to the one described for the conventional method.
The reaction flask containing phenol (0.094 mL, 1 mmol) and
V2O5 (9 mg, 0.005 mmol) dissolved in dichloroethane 69%
HNO3 (0.063 mL, 1 mmol) was added and placed in the ultra-
sonic sonicator bath and the progress of the reaction was mon-
itored by TLC. After completion of the reaction, the reaction
mixture was filtered and washed with water. The remaining part
of the workup was similar to the one adopted for the conventional
approach. All products are characterized by comparison of their
IR, 1H-NMR, and mass spectra and also with their physical data.
The nitration of certain organic compounds with V2O5 as
catalyst in the presence of a small amount of HNO3 afforded
mononitro derivatives in very good yield (Scheme 1).
A wide range of nonactive, moderately active, and active aro-
matic compounds and heterocyclic compounds are chosen for
nitration under conventional and nonconventional conditions;
corresponding results are presented in Table 2. The data re-
veal that nitration of aromatic compounds underwent smoothly
with good regioselectivity in the presence of V2O5, leading to
long reaction times (8–12 h) and good yields. It is of interest
to note that para-substituted compounds (entries 3, 5, 7, 8, 13,
and 15–18) underwent nitration only at the ortho position, while
Typical Experimental Procedure for Microwave-Assisted
Nitration (MWANR) of Organic Compounds
The microwave (MW) reactor used was of CEM make, which
was equipped with temperature, pressure, and MW power con-
trol units. An oven-dried MW vial was charged with a mixture
containing aromatic compound, V2O5 (9 mg, 0.005 mmol) and
69% HNO3 (0.063 mL, 1 mmol) and silica gel slurry, and irra-
diated in a MW (power input 140 W) at 150◦C for few minutes.
After completion of the reaction, as ascertained by TLC, the re-
action mixture was treated with sodium bicarbonate; the organic
layer was diluted with dichloromethane (DCM) and separated
from aqueous layer. The crude product mixture was purified
with ethyl acetate DCM mixture. The purity was checked with
TLC. The products were identified by characteristic spectro-
scopic data.
SCH. 1. Nitration of aromatic compounds in presence of V2O5.

NITRATION OF AROMATIC COMPOUNDS IN THE PRESENCE OF V2O5
923
TABLE 2
Nitration of aromatic compounds in presence of V2O5
Conventional
Sonication
Microwave
RT (sec) Yield (%)
S. No.
1
Substrate
Product
0RT (hrs)
Yield (%)
80
RT (min)
Yield (%)
84
08
30
90
87
2
3
08
80
80
30
80
82
90
82
07
30
90
83
4
5
08
08
75
78
30
30
80
78
90
90
80
80
6
7
08
08
75
75
30
30
80
77
90
90
82
78
8
9
08
08
78
75
30
30
80
78
90
90
81
78
(Continued on next page)

924
N. VENKATESHAM ET AL.
TABLE 2
Nitration of aromatic compounds in presence of V2O5 (Continued)
Conventional
Sonication
Microwave
S. No.
Substrate
Product
0RT (hrs)
Yield (%)
72
RT (min)
Yield (%)
76
RT (sec)
Yield (%)
75
10
08
08
30
90
11
70
30
72
90
72
12
13
09
12
68
30
60
72
90
75
62
65
180
68
14
15
10
10
64
70
45
30
70
72
120
100
70
75
16
17
09
09
68
76
30
30
72
76
90
90
75
80
18
09
70
30
72
90
80

NITRATION OF AROMATIC COMPOUNDS IN THE PRESENCE OF V2O5
925
ortho-substituted compounds (entries 2, 6, and 14) afforded para nitration reactions. The developed methods have several advan-
derivatives in very good yield. Even though benzene failed to tages such as simple workup procedure, good regioselectivity,
undergo nitration, it is also of interest to note that aromatic hy- short reaction times, and high product yields. Longer reaction
drocarbons, such as anthracene, naphthalene, α-naphthol, and times of conventional methods (8–10 h) reduced remarkably to
β-naphthol underwent smooth nitration with fairly good yields. about 30 min (0.50 h) in sonicated and 90 s (< 2 min) in case
When this protocol was extended to carbonyl compounds, ni- of MWAR. It is noteworthy to mention here that if the ortho po-
tration underwent smoothly without oxidation on any side. The sition is engaged, p-nitro derivatives are obtained while o-nitro
reaction was clean, no attack being observed on the alkyl por- derivatives are obtained when para position is engaged.
tion of the ketones. To check the regioselectivity of the reaction,
the reaction is carried out with different para-substituted aro-
SPECTROSCOPIC DATA
matic carbonyl and related compounds, which afforded only
metanitrated products in good yield.
1. 2-Nitrophenol: 1H NMR (300 MHz, CDCl3) δ 9.52 (s, 1H),
8.15 (dd, J = 8.5Hz, J = 8 Hz, 1H), 8.12 (d, J = 8 Hz, 1H),
7.55 (dd, J = 8 Hz J = 7.5 Hz, 1H) 6.95 (d, J = 8.5 Hz,
1H); ESI-MS m/z = 139.
To obtain further advantage of this protocol, the reactions are
conducted under nonconventional activation techniques, such
as ultrasonically assisted and MW-assisted methods because ul-
trasonically assisted reactions (USAR) MWAR have become a
stimulus to physical and organic chemists because of their im-
mense importance to promote and enhance a broad spectrum
of synthetic organic reactions.[14–17] The use of these nontradi-
tional tools have been found to be of great help in overcoming
many of the difficulties associated with conventional reactions
and afford several related and environmental advantages.[18] All
the reactions underwent dramatic rate enhancements followed
by achieving the selectivity with ease of experimental manipu-
lation. The reaction times reduced from 8 to 12 h (under conven-
tional conditions) to about 30 min in USA reactions and about
90 s in MWA reactions.
Rate accelerations of the ultrasonically assisted nitration re-
actions (USNR) in the present study are due to cavitation, a
physical process that creates, enlarges, and implodes gaseous
and vaporous cavities in an irradiated liquid.[14–16] Cavitation is
a process in which mechanical activation destroys the attractive
forces of molecules in the liquid phase. Applying ultrasound,
the compression of the liquid is followed by rarefaction (expan-
sion), in which a sudden pressure drop forms small, oscillat-
ing bubbles of gaseous substances. These bubbles expand with
each cycle of the applied ultrasonic energy until they reach an
unstable size; they can then collide and/or violently collapse.
Cavitation induces very high local temperatures in the liquid as
well as enhanced mass transfer.
2. 2-Me- 4-NO2 phenol: 1H NMR (300 MHz, CDCl3) δ 10.55
(s, 1H), 8.25 (dd, J = 8.5 Hz, J = 7.5 Hz, 1H), 8.12 (d, J =
8.5 Hz, 1H), 2.35 (s, 3H), 6.85 (d, J = 8.5 Hz, 1H); ESI-MS
m/z = 153.
3. 2-NO2 4-Me phenol: 1H NMR (300 MHz, CDCl3) δ 10.42
(s, 1H), 7.92 (s, 1H), 7.32 (d, J = 8 Hz, 1H), 7.12 (d, J =
8 Hz, 1H), 2.42 (s, 3H); ESI-MS m/z = 153.
4. 3-Me- 6-NO2 phenol: 1H NMR (300 MHz, CDCl3) δ10.86
(s, 1H), 8.12 (d, J = 8 Hz, 1H), 7.16 (d, J = 8 Hz, 1H),
6.64 (s 1H) 2.32 (s, 3H); ESI-MS m/z = 153.
1
5. 4-Cl-2-NO2 phenol: H NMR (300 MHz, CDCl3) δ10.54
(s, 1H), 7.82 (d, J = 8 Hz, 1H), 8.36 (s 1H) 7.12 (d, J =
8 Hz, 1H); ESI-MS m/z = 174.
1
6. 4-NO2 2-Cl phenol: H NMR (300 MHz, CDCl3) δ10.66
(s, 1H), 8.34 (s, 1H), 8.12 (d, J = 8.5 Hz, 1H), 7.15(d, J =
8.5 Hz, 1H); ESI-MS m/z = 174.
7. 2-NO2 4-Br Phenol: 1H NMR (300 MHz, CDCl3) δ10.45
(s, 1H), 8.25(s, 1H), 7.72(d, J = 8 Hz, 1H), 7.10(d, 1H, J
= 8 Hz, 1H); ESI-MS m/z = 218.
1
8. 2- NO2 Benzene-1, 4-diol: H NMR (300 MHz, CDCl3)
δ10.26(s, 2H), 7.14(d, J = 8.5 Hz, 1H), 6.92(d, J = 8.5 Hz,
1H), 7.48(s, 1H); ESI-MS m/z = 155.
9. 2- NO2–1-Naphthol: 1H NMR (300 MHz, CDCl3)
δ12.24(s, 1H), 8.58(d, J = 8.5 Hz, 1H), 8.15(d, J =
8.5 Hz, 1H), 8.05(d, J = 8.5 Hz, J = 4Hz, 1H),
7.76(m, J = 8.5 Hz J = 7.25Hz, 1H), 7.66(m, 1H,
J = 8 Hz, J = 7.25 Hz, 1H),, 7.44(d, J = 9 Hz, 1H);
ESI-MS m/z = 189.
On the other hand, the observed rate and yield enhancements
in MWA reactions[17] were attributed to the bulk activation of
molecules due to the selective absorption of MW energy by polar
molecules, nonpolar molecules being inert to the MW dielectric
loss. This point can be further supported from the fact that the
rate of the reaction has a direct dependence on the fraction of
activated/energized species.
10. NO2–2-Naphthol: 1H NMR (300 MHz, CDCl3) δ12.18(s,
1H), 8.65(d, J = 9 Hz, 1H), 8.10(m, J = 7.75 Hz, J = 5 Hz,
1H), 7.80 (m, J = 8.25 Hz J = 7.25 Hz, 1H), 7.68(d,
J = 8.25 Hz J = 5 Hz, 1H), 7.58 (m, J = 7.5 Hz, J
= 7.25 Hz, 1H), 7.20(d, J = 9 Hz, 1H); ESI-MS m/z =
189.
11. 4-Cl-3- NO2 benzaldehyde: 1H NMR (300 MHz, CDCl3)
δ 10.16 (s, 1H), 8.22 (s, 1H), 7.90 (d, J = 3.1 Hz, 1H), 7.55
(d, J = 3.1 Hz, 1H); ESI-MS m/z = 185.
CONCLUSIONS
In conclusion, the authors have demonstrated vanadium pen-
toxide as an efficient catalyst for regioselective nitration of
organic compounds under conventional and nonconventional 12. 3-OH-4 NO2 acetophenone: 1H NMR (300 MHz, CDCl3)
conditions such as ultrasonically assisted (USAR) and MWAR
δ 10.68 (s, 1H), 8.10 (m, J = 8.5 Hz, J = 3.5 Hz, 1H), 7.62

926
N. VENKATESHAM ET AL.
(d, J = 8.5 Hz, 1H), 7.52 (d, J = 3.5 Hz, 1H), 2.38 (s, 3H);
ESI-MS m/z = 181.
8. Olah. G.A.; Malhotra. R.; Narang. S.C. Nitration: Methods and Mechanism;
VCH: New York, 1989.
9. (a) Schofield, K. Aromatic Nitrations; Cambridge University Press: Cam-
bridge, 1980. (b) Ridd, J.H. Acc. Chem. Res. 1971, 4, 248.
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and Chemistry; VCH Publishers: New York, 1990.
11. Rajanna, K.C.; Ali, M.M.; Sana, S.; Tasneem, Saiprakash, P.K. Synthetic
Com. 2002, 32, 1351.
13. 4-NH2–2- NO2 Phenol: 1H NMR (300 MHz, CDCl3)
9.92 (s, 1H) 7.24 (s, 1H), 6.76 (d, J = 8 Hz, 1H),
6.82 (d, J = 8 Hz, 1H), δ 4.45 (s, 2H); ESI-MS m/z =
154.
14. 2-OH 5-NO2 Benzaldehyde: 11.24δ (s 1H, OH) 10.45δ (s
1H, CHO) 7.18δ (d 1H, J = 8 Hz) 8.36δ (d 1H, J = 8 Hz),
8.72δ (s 1H); m/z = 167
12. Rajanna, K.C.; Satish Kumar, M.; Venkanna, P.; Ramgopal, S.;
Venkateswarlu, M. Int. J. Org. Chem. 2011, 1, 250.
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Veerasomaiah, P. Int. J. Org. Chem. 2012, 2, 254. (c) Abdulla; Amina, S.;
Arun Kumar, Y.; Arifuddin, M.; Rajanna, K.C. Synth. Comm. 2011, 41,
2946. (d) Sana, S.; Rajanna, K.C.; Rajendar Reddy, K.; Bhooshan, M.;
Venkateswarlu, M.; Satish Kumar, M.; Uppalaiah, K. Green. Sust. Chem.
2012, 2, 97. (e) Srinivas, P.; Rajanna K.C.; Satish Kumar, M.; Rajendar
Reddy, K. Synth. React. Inorg. Metal-Org. Nanomet. Chem. 2013, 44, 364.
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Low, C.M.R. Ultrasound in Synthesis; Springer: Berlin, 1989. (c) Richards,
W.T.; Loomi, A.L. J. Am. Chem. Soc. 1927, 49, 3086.
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15. 4-OH 3-NO2 Benzaldehyde: 11.28δ (s 1H, OH) 10.34δ (s
1H, CHO) 7.26δ (d6, 1H, dd, J = 7.5 Hz) 7.64δ (d 1H, d J
= 7.5 Hz) 8.38δ (s 1H); m/z = 167
16. 4-Cl-3- NO2 benzaldehyde: 1H NMR (300 MHz, CDCl3) δ
10.16 (s, 1H), 8.22 (s, 1H), 7.90 (d, J = 3.1 Hz, 1H), 7.55
(d, J = 3.1 Hz, 1H); ESI-MS m/z = 185.
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