Preparation and characterization of nano-Co-[4-chlorophenyl-salicylaldimine-methyl pyranopyrazole]Cl2 as a new Schiff base complex and catalyst for the solvent-free synthesis of 1-amidoalkyl-2-naphthols

Article abstract of DOI:10.1002/aoc.5252

By the reaction of 4-chlorobenzaldehyde with ethyl acetoacetate, malononitrile, and hydrazine hydrate, 6-amino-4-(4-chlorophenyl)-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile was prepared and then reacted with salicylaldehyde and CoCl₂

Full text of DOI:10.1002/aoc.5252

Received: 25 May 2019
DOI: 10.1002/aoc.5252
Revised: 12 August 2019
Accepted: 1 September 2019
F U L L P A P E R
Preparation and characterization of nano-
Co-[4-chlorophenyl-salicylaldimine-methyl pyranopyrazole]
Cl2 as a new Schiff base complex and catalyst for the
solvent-free synthesis of 1-amidoalkyl-2-naphthols
Ahmad Reza Moosavi-Zare
| Hamid Goudarziafshar
| Fatemeh Nooraei
Department of Chemistry, University of
Sayyed Jamaleddin Asadabadi, Asadabad,
6541861841, Iran
Abstract
By the reaction of 4-chlorobenzaldehyde with ethyl acetoacetate,
malononitrile, and hydrazine hydrate, 6-amino-4-(4-chlorophenyl)-3-methyl-2,
4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile was prepared and then reacted
with salicylaldehyde and CoCl2Á6H2O to produce nano-Co-[4-cholorophenyl-
salicylaldimine-methylpyranopyrazole]Cl2 (nano-[Co-4CSMP]Cl2). The pre-
pared nano-Schiff base complex was reported for the first time and fully
characterized by Fourier transform-infrared spectroscopy, thermal gravimetric
analysis, differential thermal gravimetric analysis, scanning electron micros-
copy, energy-dispersive X-ray spectroscopy, transmission electron microscopy,
and Brunner–Emmett–Teller analyses and applied as an efficient catalyst for
the synthesis of some 1-amidoalkyl-2-naphthol derivatives.
Correspondence
Ahmad Reza Moosavi-Zare and Hamid
Goudarziafshar, Sayyed Jamaleddin
Asadabadi University, Asadabad,
6541861841, I. R. Iran.
Email: moosavizare@yahoo.com;
hamid_gafshar@yahoo.com
Funding information
sayyed jamaleddin asadabadi university
K E Y W O R D S
1-amidoalkyl-2-naphthol, nano-[co-4CSMP]Cl2, pyranopyrazole, Schiff base
1-aminoalkyl-2-naphthols[5–7] and 1,3-oxazine derivatives.[8]
In particular, 1,3-oxazine derivatives exhibit some significant
activities, including antibiotic,[9] antitumor,[10] analgesic,[11]
1 | INTRODUCTION
Azomethine compounds, namely, Schiff bases, are pre-
pared by the reaction of primary amine with carbonyl
compounds such as aldehydes or ketones. Schiff base com-
pounds are widely introduced as one of the useful kinds of
ligands due to their easy and convenient way for the prepa-
ration of materials and their interesting coordination
chemistry.[1] Schiff base complexes were prepared by the
coordination of Schiff base ligands with different metals.
These compounds possess some important activities such
as antibacterial, antifungal, anticancer, antioxidant, anti-
inflammatory, antimalarial, and antiviral properties.
Schiff base complexes are also used as efficient catalysts in
organic transformations.[2–4] 1-Amidoalkyl-2-naphthol
derivatives are beneficial compounds due to their ability to
convert into some biological materials such as
anticonvulsant,[12]
antipsychotic,[13]
antimalarial,[14]
antianginal,[15] antihypertensive,[16] and antirheumatic prop-
erties.[17] One-pot three-component condensation reactions
of different phenols with aromatic aldehydes and amide
derivatives were reported in the presence of various catalysts
such as [Msim]Cl, [Dsim]Cl, [Msim]AlCl4,[18,19] trityl
chloride,[20,21] saccharin sulfonic acid,[22] nano SnO2,[23] and
[Msim]FeCl4.[24] Because of the significance of these com-
pounds in various applications and some limitations in previ-
ous approaches, the methods proposed herein will be useful
are still required.
Recently, we have prepared a new category of Schiff
base ligands, by the reaction of various pyranopyrazole
derivatives with salicylaldehyde, and then mixed the
The synthesis of 1-amido alkyl 2-naphthols. 2019;e5252.
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https://doi.org/10.1002/aoc.5252

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MOOSAVI-ZARE ET AL.
ligand with different metals to prepare Schiff base com-
plexes. These complexes were studied and their catalytic
activity was tested during the synthesis of various com-
pounds such as pyrano[2,3-d] pyrimidinediones,[25]
4-[(2-hydroxynaphthalen-1-yl)(aryl)methyl]-5-methyl-
2-phenyl-1H-pyrazol-3(2H)-ones,[26] pyranopyrazoles,[27]
hexahydroquinolines,[28,29] and bis (pyrazolyl)methanes.[30]
In continuation of our previous investigations on the
designing of new Schiff base complexes and their catalytic
application in the synthesis of various organic compounds,
we have now prepared nano-Co-[4-cholorophenyl-sal-
icylaldimine-methylpyranopyrazole]Cl2 (nano-[Co-4CSMP]
Cl2) as a new Schiff base complex and successfully tested it
as a catalyst in the synthesis of 1-amidoalkyl-2-naphthol
derivatives (Figure 1 and Scheme 1).
(0.1 mmol, 0.0123 g, 10 mol%) was added into a 10-mL
round-bottomed flask connected to a reflux condenser,
and stirred at 85 ꢀC for 5 min, and then 4-chlo-
robenzaldehyde (1 mmol) and malononitrile (0.066 g,
1 mmol) were added to the reaction mixture. Upon com-
pletion of the reaction, followed by thin-layer chromatog-
raphy, the reaction mixture was cooled down to room
temperature. Water was added to the reaction mixture
that was then dissolved with isonicotinic acid. Finally,
the aqueous layer was separated from the reaction mix-
ture, and the solid residue (crude product) was triturated
using a mixture of ethanol and water (9:1) to prepare
6-amino-4-(4-chlorophenyl)-3-methyl-2,4-dihydropyrano
[2,3-c]pyrazole-5-carbonitrile as an amine.[31] The pre-
pared amine (1 mmol) and CoCl2Á6H2O (1 mmol) were
added into a 25-mL round-bottomed flask containing
salicylaldehyde (1.5 mmol), which was connected to a
2 | EXPERIMENTAL
ꢀ
reflux condenser, and stirred at 100 C for 72 hr. Finally,
the reaction mixture was washed with ethyl acetate three
times to purify nano-[Co-4CSMP]Cl2 from excess
salicylaldehyde (Scheme 2).
All chemicals were purchased from Merck or Fluka
Chemical Companies. The known products were identi-
fied by comparison of their melting points (MPs) and
spectral data with those reported in the literature. The
1H-nuclear magnetic resonance (1H-NMR; 500 MHz) and
13C-NMR (125 MHz) spectra were recorded on a Bruker
AVANCE DPX FT-NMR spectrometer (δ in ppm). Infra-
red (IR) spectrum of products was recorded by Perkin
Elmer PE-1600-FTIR.
2.2 | General procedure for the synthesis
of 1-amidoalkyl-2-naphthols
A mixture of 2-naphthol (0.288 g, 2 mmol), acetamide
(2.5 mmol), aromatic aldehyde (2 mmol), and nano-[Co-
4CSMP]Cl2 (5 mol %) was added into a 25 mL-round-bot-
tomed ꢀflask connected to a reflux condenser and stirred
at 100 C for an appropriate period. After the completion
of the reaction, as monitored by thin-layer chromatogra-
phy, the reaction mixture was cooled down to room tem-
perature and the product and remaining starting
materials were extracted with warm ethanol (20 ml) to
filter them from the catalyst (the product and remaining
starting materials are soluble in warm ethanol; however,
the catalyst is not). The product was purified by recrystal-
lization of the reaction mixture in ethanol (90%).
2.1 | Procedure for the synthesis of
nano-co-[4-cholorophenyl-salicylaldimine-
methylpyranopyrazole]Cl2 (nano-
[co-4CSMP]Cl2)
A mixture of ethyl acetoacetate (0.13 g, 1 mmol), hydra-
zine hydrate (1.25 mmol), and isonicotinic acid
2.2.1 | N-([4-(benzyloxy)phenyl]
[2-hydroxynaphthalen-1-yl]methyl)
acetamide
White solid; MP: (226–230 ꢀC); IR (KBr cm−1): 3424,
3064, 3032, 2905, 2863, 1627, 1509, 1437, 1378, 1269, 1247,
1090, 1062, 1024, 816, 742, 696, 559; H-NMR [500 MHz,
1
FIGURE 1 Structure of nano-[Co-4CSMP]Cl2
SCHEME 1 Preparation of 1-amidoalkyl-
2-naphthols

THE SYNTHESIS OF 1-AMIDO ALKYL 2-NAPHTHOLS
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SCHEME 2 Preparation of nano-[Co-4CSMP]Cl2
dimethyl sulfoxide (DMSO)-d6]: 1.95 (s, 3H, CH3), 5.02
(s, 2H), 6.88 (d, 2H, J = 8.85 Hz) 7.04–7.07 (m, 3H),
7.19–7.41 (m, 8H), 7.74 (d, 1H, J = 8.85 Hz), 7.79 (d, 1H,
J = 7.55 Hz), 7.84 (s, 1H), 8.40 (d, 1H, J = 8.45 Hz), 9.95
(s, 1H); 13C-NMR (125 MHz, DMSO-d6): 22.7, 47.4, 69.1,
114.3, 118.5, 118.9, 122.3, 126.2, 127.2, 127.6, 127.7, 128.4,
128.5, 129.1, 132.3, 134.6, 137.1, 153.0, 156.7, 169.09.
2H), 7.46 (d, 1H, J = 2.2 Hz), 7.59 (d, 1H, J = 8.5 Hz),
7.74 (d, 1H, J = 8.85 Hz), 7.79 (d, 1H, J = 8.10 Hz), 7.96
(d, 1H, J = 8.70 HZ), 8.62 (s, 1H), 9.82 (s, 1H); 13C-NMR
(125 MHz, DMSO-d6): 22.4, 47.4, 116.4, 118.7, 122.4,
122.6, 126.4, 126.5, 128.3, 128.5, 128.7, 129.7, 131.3, 131.7,
132.8, 132.9, 139.4, 153.8, 168.9.
2.2.4 | N-[(2-hydroxynaphthalen-1-yl)
(4-nitrophenyl)methyl]acetamide
2.2.2 | N-[(4-bromophenyl)
(2-hydroxynaphthalen-1-yl)methyl]
acetamide
White solid; MP: (250–254 ꢀC), IR (KBr cm−1): 3392,
3264, 3052, 2958, 1626, 1641, 1523, 1439, 1281, 853, 825,
581, 512; 1H-NMR (500 MHz, DMSO-d6): 2.02 (S, 3H,
CH3), 7.17–7.29 (m, 3H), 7.40 (d, 3H, J = 8.30 Hz), 7.81 (t,
3H, J = 8.75 Hz), 8.13 (d, 2H, J = 8.90 Hz), 8.57 (d, 1H,
J = 7.90 Hz), 10.11 (s, 1H); 13C-NMR (125 MHz, DMSO-
d6): 22.6, 48.0, 117.9, 118.5, 122.6, 123, 123.3, 123.5, 126.8,
127.2, 127.8, 128.5, 128.7, 129.9, 132.3, 145.9, 151.3,
153.4, 169.9.
White solid; MP: (220–225 ꢀC); IR (KBr cm−1): 3393,
3055, 2962, 2874, 2788, 2703, 2615, 1636, 1620, 1580,
1522, 1488, 1361, 1331, 1245, 1180, 1064, 1072, 1011,
1
934, 864, 820, 747, 680, 585, 512; H-NMR (500 MHz,
DMSO-d6): 1.99 (s, 3H, CH3), 7.07–7.09 (m, 3H),
7.11–7.29 (m, 2H), 7.36–7.39 (m, 1H), 7.44 (d, 2H,
J = 8.55 Hz), 7.76–7.81 (m, 3H), 8.46 (d, 1H, J = 8.2 HZ),
10.04 (s, 1H); 13C-NMR (125 MHz, DMSO-d6): 22.7, 47.6,
118.4, 118.5, 119.2, 122.5, 126.5, 128.4, 128.5, 128.6, 128.7,
129.5, 130.9, 131.2, 132.3, 142.3, 153.3, 169.5.
2.2.5 | N-[(2-hydroxynaphthalen-1-yl)
(3-nitrophenyl)methyl]acetamide
White solid; MP: (245–250 ꢀC); IR (KBr cm−1): 3375,
3226, 3087, 3063, 1648, 1630, 1579, 1525, 1530, 1350,
1209, 1094, 990, 806, 734, 584; 1H-NMR (500 MHz,
DMSO-d6): 2.01 (s, 3H, CH3), 7.17 (d, 1H, J = 7.9 Hz),
7.22 (d, 1H, J = 8.8 Hz), 7.29 (t, 1H, J = 7.5 Hz),
7.39–7.42 (m, 1H), 7.54 (m, 2H), 7.80–7.84 (m, 3H), 8.00
(s, 1H), 8.05 (d, 1H, J = 7.25 Hz), 8.64 (d, 1H,
J = 8.00 Hz), 10.16 (S, 1H, OH); 13C-NMR (125 MHz,
DMSO-d6): 22.4, 47.5, 117.7, 118.3, 120.3, 121.1, 122.5,
122.7, 126.7, 128.3, 128.6, 129.5, 129.8, 132.08, 132.7,
145.3, 147.6, 153.3, 169.6.
2.2.3 | N-[(2,4-dichlorophenyl)
(2-hydroxynaphthalen-1-yl)methyl]
acetamide
White solid; MP: (200–202 ꢀC); IR (KBr cm−1): 3406,
3143, 3067, 1650, 1632, 1582, 1517, 1471, 1439, 1370,
1322, 1298, 1267, 1164, 1147, 1089, 1063, 986, 942,
1
870, 816, 750, 750, 583, 458; H-NMR (500 MHz, DMSO-
d6): 1.93 (s, 3H, CH3), 7.00 (d, 1H, J = 7.85 Hz), 7.11 (d,
1H, J = 8.85 HZ), 7.27 (t, 1H, J = 7.75 Hz), 7.39–7.45 (m,

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MOOSAVI-ZARE ET AL.
malononitrile, and hydrazine hydrate, 6-amino-
4-(4-chlorophenyl)-3-methyl-2,4-dihydropyrano[2,3-c]
pyrazole-5-carbonitrile was prepared according to a previ-
ous study.[31] The prepared pyranopyrazole was then
reacted with salicylaldehyde and CoCl2Á6H2O to produce
nano-Co-[4-cholorophenyl-salicylaldimine-
methylpyranopyrazole]Cl2 (nano-[Co-4CSMP]Cl2) as a
nano-Schiff base complex (Scheme 2). The structure of
nano-[Co-4CSMP]Cl2 was studied by IR, scanning elec-
tron microscopy, energy-dispersive X-ray spectroscopy
(EDX), transmission electron microscopy (TEM),
Brunner-Emmett-Teller (BET), thermogravimetric analy-
sis, and derivative thermogravimetry analyses.
2.2.6 | N-[(4-chlorophenyl)
(2-hydroxynaphthalen-1-yl)methyl]
acetamide
White solid; MP: (230–232 ꢀC); IR (KBr cm−1): 3393,
3268, 3055, 2962, 2870, 2789, 2703, 2616, 1638, 1625,
1581, 1515, 1492, 1439, 1332, 1374, 1362, 1332, 1279,
1
1245, 1172, 1092, 1064, 1014, 934, 848, 819, 748, 500; H-
NMR (500 MHz, DMSO-d6): 1.98 (s, 3H, CH3), 7.09 (d,
1H, J = 8.20 Hz), 7.15 (d, 2H, J = 8.45 Hz), 7.22 (d, 1H,
J = 8.85 Hz), 7.25–7.39 (m, 4H), 7.76–7.81 (m, 3H), 8.46
(d, 1H, J = 8.25 Hz), 10.03 (s, 1H, OH); 13C-NMR
(125 MHz, DMSO-d6): 22.6, 47.5, 118.4, 118.5, 122.5,
126.5, 127.9, 128.2, 128.3, 128.5, 128.6, 129.5, 130.7, 132.3,
141.8, 153.2, 169.5.
First, 4CSMP as a Schiff base was synthesized alone
1
and its structure was studied by H-NMR and 13C-NMR
spectra (Schemes S1 and S2). After the preparation of
nano-[Co-4CSMP]Cl2 by the reaction of 4CSMP with
CoCl2Á6H2O, EDX images from nano-[Co-4CSMP]Cl2
were studied, which further confirmed the successful
preparation of the catalyst. According to EDX analysis,
3 | RESULTS AND DISCUSSION
For the synthesis of nano-[Co-4CSMP]Cl2, by the reac-
tion of 4-chlorobenzaldehyde with ethyl acetoacetate,
FIGURE 2 Energy-dispersive X-ray
spectroscopy of nano-[Co-4CSMP]Cl2

THE SYNTHESIS OF 1-AMIDO ALKYL 2-NAPHTHOLS
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FIGURE 3 Infrared spectrum of nano-[Co-4CSMP]Cl2
FIGURE 4 Scanning electron microscopy
image of nano-[Co-4CSMP]Cl2
FIGURE 5 Transmission electron micrographs of nano-[Co-4CSMP]Cl2

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MOOSAVI-ZARE ET AL.
TABLE 1 Specific surface area (SBET), diameter pore, and
total pore volume of nano-[Co-4CSMP]Cl2
Brunner–Emmett–Teller
Pore
(BET) surface area
Diameter volume
Sample
(m2 g−1
)
(nm)
(cm3 g−1
)
Nano-[Co- 16.042
4CSMP]
1.88
0.07
Cl2
the desired elements, namely, carbon, oxygen, nitrogen,
chlorine, and cobalt, were found in the structure of the
catalyst (Figure 2).
The IR spectrum of nano-[Co-4CSMP]Cl2 showed a
broad peak at 2900–3600 cm–1, which could be attributed
to the O–H stretching of the OH group and the peak
which appeared at 1666 cm–1 to the stretching mode of
C=N bond of azomethine (Figure 3). To demonstrate the
steps involved in the synthesis of nano-[Co-4CSMP]Cl2 as
a Schiff base complex, the IR spectra of 6-amino-
4-(4-chlorophenyl)-3-methyl-2,4-dihydropyrano[2,3-c]
pyrazole-5-carbonitrile as an amine and 4CSMP as an
imine were compared with nano-[Co-4CSMP]Cl2
(Figure 3). When cobalt coordinates with imine, the peak
at 2208 cm–1 related to the CN bond is omitted,
suggesting that the cobalt has interacted with the CN
group and changed the triple bond in CN (Figure 3). An
analysis of scanning electron microscopy images of nano-
[Co-4CSMP]Cl2 also confirmed the formation of nano-
sized catalyst particles (Figure 4).
FIGURE 7 Thermal gravimetric analysis and differential
thermal analysis (DTA) of nano-[Co-4CSMP]Cl2
The size of nano-[Co-4CSMP]Cl2 was also studied by
TEM analysis. TEM measurements further confirmed
that the particles prepared were nano sized (Figure 5).
Because the catalyst prepared has a porous structure, the
volume and size of the cavities contained in it were inves-
tigated. The BET surface area, pore size, and pore volume
of nano-[Co-4CSMP]Cl2 are 16.042 m2 g–1, 1.88 nm, and
0.07 cm3 g–1, respectively (Table 1 and Figure 6).
Thermogravimetric analysis and differential thermal
analysis of nano-[Co-4CSMP]Cl2 were also performed,
with the corresponding results presented in Figure 7. The
ꢀ
nano-[Co-4CSMP]Cl2 decomposed after 200 C, which is
clearly seen in the figure.
To optimize the reaction condition, the reaction of 2-
naphthol (2 mmol) with 4-chlorobenzaldehyde (2 mmol)
and acetamide (2.4 mmol) was selected as the model
TABLE 2 Effect of nano-[Co-CSMP]Cl2 amounts, temperature,
and solvent on the reaction between β-naphthol with
4-chlorobenzaldehyde and acetamide
Mol%
of
catalyst Solvent
Temp.
(ꢀC)
Time
(min)
Yielda
(%)
—
3
—
100
100
120
5
—
64
90
90
45
80
74
80
85
—
5
—
100
5
8
—
100
5
5
—
50
40
20
5
5
—
80
5
—
120
5
H2O
Ethanol
Reflux
Reflux
25
20
FIGURE 6 Nitrogen adsorption (ADS)–desorption (DES)
5
isotherms of nano-[Co-4CSMP]Cl2
aIsolated yield.

THE SYNTHESIS OF 1-AMIDO ALKYL 2-NAPHTHOLS
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TABLE 3 Synthesis of 1-amidoalkyl-2-naphthols using nano-[Co-4CSMP]Cl2
Time
(min)
Yielda
(%)
Melting point (ꢀC;
literature value)
Entry
Product
1
15
90
246–248 (238–240)[18]
2
3
5
5
95
225–227 (223–225)[18]
90
252–253 (260–262)[32]
4
5
6
10
90
85
90
195–199 (197–199)[18]
237–239 (237–238)[33]
225–227 (220–222)[18]
5
5
7
10
95
200–202 (206–208)[32]
8
9
5
85
90
230–232 (229–229.5)[34]
10
222–225 (226–228)[18]
(Continues)

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MOOSAVI-ZARE ET AL.
TABLE 3 (Continued)
Time
(min)
Yielda
(%)
Melting point (ꢀC;
literature value)
Entry
Product
10
15
85
200–204 (190–191)[33]
11
12
10
90
95
245–246 (250–252)[35]
235–237 (246–248)[18]
5
13
14
5
80
90
245–250 (238–240)[18]
246–250 (245–246)[34]
10
15
5
90
230–235
aIsolated yield.
reaction and tested in the presence of different amounts
of catalyst, at 50–100 ꢀC under solvent-free condition
(Table 2). As shown in Table 2, the best result was
obtained using 5 mol% of catalyst at 100 ꢀC. Furthermore,
to show the superiority of the solvent-free condition, the
model reaction was tested in the presence of various
solvents such as H2O and ethanol in which the yield of
product was lower than that in the solvent-free condition.
Moreover, the model reaction was tested in the absence
of catalyst, in which no progress in reaction was noted
(Table 2).
In the next step, the reaction of 2-naphthol with vari-
ous aryl aldehydes and acetamide was examined in the
presence of nano-[Co-4CSMP]Cl2 at 100 ꢀC and in
the absence of solvent to estimate the domain and the
generality of the catalysts. Aryl aldehydes containing
electron-releasing substituents, electron-withdrawing
substituents, and halogens on their aromatic rings
reacted successfully in the reaction, and afforded the
expected products in acceptable yields and reaction
times (Table 3).
According to the proposed mechanism of reaction and
based on the previous literature,[32–44] first, aromatic
aldehyde is activated by the catalyst and reacted with
2-naphthol to afford I. In the next step, orthoquinone
methide (II) is prepared by the elimination of one mole-
cule of water from I. Finally, by Michael addition of
acetamide, which is activated with the catalyst, II affords
the expected 1-amidoalkyl-2-naphthol (Scheme 3).
To compare the applicability and the efficiency of
nano-[Co-4CSMP]Cl2 with previously reported catalysts
for the synthesis of 1-amidoalkyl-2-naphthols, the results
of using these catalysts in the reaction of 2-naphthol with
4-chlorobenzaldehyde and acetamide are summarized in

THE SYNTHESIS OF 1-AMIDO ALKYL 2-NAPHTHOLS
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SCHEME 3 Proposed mechanism for the
preparation of 1-amidoalkyl-2-naphthols
TABLE 4 Comparison of the results of the reaction of 2-naphthol with 4-chlorobenzaldehyde and acetamide catalyzed by
nano-[Co-4CSMP]Cl2 with some previously reported catalysts
Catalyst
amount
(mol%)
Turnover
Time
(min)
Yield
(%)
frequencya
Catalyst and temperature
Nano-[Co-4CSMP]Cl2, 100 ꢀC
Cyanuric chloride, 100 ꢀC
H3PW12O40, 100 ꢀC
(min–1
)
Ref.
5
10
2
5
10
80
10
90
90
88
85
3.6
This work
[36]
0.9
[37]
[38]
0.55
1.7
N-(4-sulfonic acid)butyl triethylammonium hydrogen
sulfate, 120 ꢀC
5
[39]
[40]
[41]
[42]
[43]
Cu1.5PW12O40, 100 ꢀC
H3BO3, 120 ꢀC
2
80.8
20
10
10
5
90
15
30
6
78
72
87
90
91
61
0.433
0.059
0.145
1.500
0.505
0.630
ZnO nanoparticles, 120 ꢀC
Phthalimide-N-sulfonic acid, 100 ꢀC
Citric acid, 120 ꢀC
18
20
CoCl2Á6H2O, 100 ꢀC
aTurnover frequency.
This work
Table 4. The presented catalyst remarkably improved the
synthesis of 1-amidoalkyl-2-naphthols in terms of reac-
tion time, yield, and turnover frequency. This reaction
was also performed in the presence of CoCl2Á6H2O alone;
however, compared with the reaction performed over
Cl2) as a Schiff base complex and efficient catalyst for the
synthesis of 1-amidoalkyl-2-naphthols by the condensa-
tion reaction of 2-naphthol with various aryl aldehydes
and acetamide at 100 ꢀC under solvent-free conditions.
ꢀ
ACKNOWLEDGEMENTS
nano-[Co-4CSMP]Cl2 at 100 C under solvent-free condi-
tions, there was no improvement in results and the reac-
tion overall was weaker (Table 4).
The authors gratefully acknowledge Sayyed Jamaleddin
Asadabadi University for providing support to this work.
4 | CONCLUSIONS
ORCID
We have introduced nano-Co-[4-cholorophenyl-salicylal-
Ahmad Reza Moosavi-Zare https://orcid.org/0000-
dimine-methylpyranopyrazole]Cl2
(nano-[Co-4CSMP]
0003-0321-9326

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MOOSAVI-ZARE ET AL.
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Hamid Goudarziafshar https://orcid.org/0000-0002-
5930-6253
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SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of this
article.
How to cite this article: Moosavi-Zare AR,
Goudarziafshar H, Nooraei F. Preparation and
characterization of nano-Co-[4-chlorophenyl-
salicylaldimine-methyl pyranopyrazole]Cl2 as a
new Schiff base complex and catalyst for the
solvent-free synthesis of 1-amidoalkyl-2-naphthols.
Appl Organometal Chem. 2019;e5252. https://doi.
org/10.1002/aoc.5252