1-Butyl-1-methylpyrrolidinium hydrogen sulfate-promoted preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives

Article abstract of DOI:10.1007/s11164-012-0749-9

A convenient preparative approach for synthesis of various 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones promoted by 1-butyl-1- methylpyrrolidinium hydrogen sulfate is developed which involves cyclocondensation of aldehydes with amines and ethyl pyruvate under ambient conditions. Graphical abstract: A convenient preparative approach for synthesis of various 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones promoted by 1-butyl-1-methylpyrrolidinium hydrogen sulfate is developed which involves cyclocondensation of aldehydes with amines and ethyl pyruvate under ambient conditions.[Figure not available: see fulltext.]

Full text of DOI:10.1007/s11164-012-0749-9

Res Chem Intermed
DOI 10.1007/s11164-012-0749-9
1-Butyl-1-methylpyrrolidinium hydrogen sulfate-
promoted preparation of 1,5-diaryl-3-(arylamino)-
1H-pyrrol-2(5H)-one derivatives
Majid Ghashang
Received: 29 June 2012 / Accepted: 25 July 2012
Ó Springer Science+Business Media B.V. 2012
Abstract A convenient preparative approach for synthesis of various 1,5-diaryl-3-
(arylamino)-1H-pyrrol-2(5H)-ones promoted by 1-butyl-1-methylpyrrolidinium hydro-
gen sulfate is developed which involves cyclocondensation of aldehydes with amines
and ethyl pyruvate under ambient conditions.
Keywords 1,5-Diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one Á c-Lactam Á
Ionic liquid Á 1-Butyl-1-methylpyrrolidinium hydrogen sulfate
Introduction
Synthesis of pyrroles and their analogs has been an area of interest for chemists
as well as biologists because these are versatile precursors for synthesis of
pharmacologically significant molecules and natural products [1–6]. A useful class
of pyrrole skeletons is 1,5-dihydro-2H-pyrrol-2-ones, which are an appealing family
of lactams. These compounds and their 3-amino substituents (which also can act as
enamine) are used increasingly as valuable intermediates in organic synthesis and
offer major synthetic opportunities in synthesis of biological and pharmaceutical
compounds [1–6]. Accordingly, many methods for assembly of 1,5-diaryl-3-
(arylamino)-1H-pyrrol-2(5H)-ones have been developed which involve two-com-
ponent condensation of amines with pyrrolidine-2,3-diones [7] and b,c-unsaturated
a-oxo esters [8] or tricomponent reaction of amines, aldehyde, and pyruvate using
acidic catalysts such as H2SO4 [9], thiourea and phosphoric acid analogs [10], SiO2–
FeCl3 [11], and triethylammonium hydrogen sulfate [12].
M. Ghashang (&)
Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University,
P.O. Box 517, Najafabad, Esfahan, Iran
e-mail: ghashangmajid@gmail.com
123

M. Ghashang
CH3
N
HSO4
CH3
NHAr'
O
N
Ar'
O
OEt
+ ArCHO + Ar'NH2
Ar
r.t.; EtOH
O
Scheme 1 Preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives
In recent years, use of ionic liquid media in organic chemistry has gained
considerable attention because these reactions are attractive in terms of procedural
simplicity and high product yield. This also contributes towards development of
clean and green chemical processes and investigations of new and efficient catalysts
[13–18]. Ionic liquids have shown advantages of high thermal stability, negligible
vapor pressure, and recyclability [13–18]. As media, they have shown great promise
as an attractive alternative to conventional solvents. In many cases, the products are
weakly soluble in the ionic phase so that the products can be easily separated by
simple filtration and washing. Therefore, much attention is currently being focused
on organic reactions promoted by ionic liquids.
The overall aim of this project is to develop and validate an efficient protocol for
synthesis and easy purification of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones
from cyclocondensation reaction of aldehydes, aryl amines, and ethyl pyruvate in
the presence of 1-butyl-1-methylpyrrolidinium hydrogen sulfate as an efficient
acidic ionic liquid (for the preparation of 1-butyl-1-methylpyrrolidinium hydrogen
sulfate, see [19–21]) (Scheme 1).
Results and discussion
To study the effect of solvent, the reaction of benzaldehyde, 4-methylaniline, and
ethyl pyruvate was examined in different solvents (Table 1, entries 1–7) and
solvent-free condition (Table 1, entry 8). 1-Butyl-1-methylpyrrolidinium hydrogen
sulfate was applied as effective promoter (Scheme 2). Among the various
solvents tested, ethanol was chosen in terms of higher yield. Then the effect of
the amount of promoter on this transformation was examined, and the results
demonstrated that 1 mmol catalyst appeared to give the optimum yield (Table 1,
entries 9–11). Thus, the best yield, cleanest reaction, and most facile workup
were achieved by employing 1 mmol catalyst in ethanol under ambient condition
(Table 1, entry 5).
To show the generality and scope of this protocol, we used various aldehydes and
amines (Scheme 1; Table 2). Notably, a wide range of aldehydes (aromatic,
heteroaromatic, and aliphatic) and aromatic amines were well permitted under the
reaction conditions (Table 2, products a–y). In all cases, aromatic aldehydes
containing electron-donating groups gave shorter times and higher yields than those
with electron-withdrawing groups. Our results show that aliphatic aldehydes react
with 4-methyl aniline and ethyl pyruvate successfully in good yield (Table 2, product
123

Preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives
Table 1 Optimization of the reaction conditions in the synthesis of 3-(p-tolylamino)-5-phenyl-1-p-tolyl-
1H-pyrrol-2(5H)-one (Scheme 2)
Entry
Catalyst (mmol)
T (°C)
Solvent (5 mL)
Yield (%)a
1
1
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
n-Hexane
CH2Cl2
Et2O
57
67
70
75
89
80
45
70
45
7
2
1
3
1
4
1
EtOAc
EtOH
MeOH
–
5
1
6
1
8
1
9
0.5
0.25
–
EtOH
EtOH
EtOH
10
11
a
Isolated yields, reaction time: 2 h
H3C
NH
NH2
O
Catalyst
OEt
+ PhCHO +
H3C
O
N
O
CH3
Scheme 2 Preparation of 3-(p-tolylamino)-5-phenyl-1-p-tolyl-1H-pyrrol-2(5H)-one
y). The reactions were clean, and all the products were easily isolated simply by
filtration and washing with diethyl ether.
The reaction of cyclohexyl amine with benzaldehyde and ethyl pyruvate failed to
give any product (Table 2, entry 23).
To explain the formationof1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones via the
one-pot multicomponent reaction, we have proposed a plausible reaction mechanism,
which is illustrated in Scheme 3. Firstly, catalytic coupling of amine with aldehyde by
Brønsted acid occurs to form intermediate a. In the same manner, ethyl pyruvate can
react with amine to form intermediate b, which is equilibrated with their enamine form
(c). Thereafter, the formation of intermediate d resulting from condensation of
intermediate a with intermediate c was established. Finally, the imine–enamine
conversion of intermediate d followed by loss of ethanol from enamine form results in
synthesis of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives (Scheme 3).
To estimate the efficiency and generality of this methodology, the result obtained
for synthesis of 3-(p-tolylamino)-5-phenyl-1-p-tolyl-1H-pyrrol-2(5H)-one by this
method was compared with those of previously reported methods. The results are
123

M. Ghashang
Yield (%)a
Table 2 Synthesis of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives
Entry
Aldehyde
Amine
Product
Time (h)
1
Benzaldehyde
4-Methylaniline
4-Methoxyaniline
4-Chloroaniline
3-Methylaniline
4-Chloroaniline
4-Chloroaniline
4-Chloroaniline
4-Chloroaniline
4-Chloroaniline
4-Methoxyaniline
4-Methoxyaniline
4-Methoxyaniline
4-Methoxyaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
3-Methylaniline
3-Methylaniline
4-Methylaniline
4-Methoxyaniline
4-Methylaniline
Cyclohexyl amine
a
b
c
d
e
f
2
2
3
2
4
3
3
3
3
3
5
2
2
3
2
2
2
2
2
4
4
2
2
89
82
88
87
79
89
82
75
84
83
69
90
91
77
93
92
88
70
89
74
72
70
–
2
Benzaldehyde
3
Benzaldehyde
4
Benzaldehyde
5
4-Chlorobenzaldehyde
4-Methoxybenzaldehyde
4-Methylbenzaldehyde
4-tert-Butylbenzaldehyde
3,4,5-Trimethoxybenzaldehyde
4-Chlorobenzaldehyde
4-Nitrobenzaldehyde
4-Methoxybenzaldehyde
4-Methylbenzaldehyde
4-Chlorobenzaldehyde
4-Methoxybenzaldehyde
4-Methylbenzaldehyde
3,4,5-Trimethoxybenzaldehyde
4-Methylbenzaldehyde
3,4,5-Trimethoxybenzaldehyde
Furfural
6
7
g
h
i
8
9
10
11
12
13
14
15
16
17
118
19
20
21
22
23
a
j
k
l
m
n
o
p
q
r
s
t
Furfural
w
y
z
Butyraldehyde
Benzaldehyde
Isolated yields. All known products have been reported previously in the literature and were charac-
terized by comparison of infrared (IR) and nuclear magnetic resonance (NMR) spectra with authentic
samples [8–12]
summarized in Table 3. It was found that the present method is convincingly
superior to the reported methods in terms of reaction time and product yield.
Our protocol uses ionic liquids during the reaction process, making it superior to
reactions that use hazardous liquid acidic catalysts.
In summary, simple one-pot three-component synthesis of 1,5-diaryl-3-(arylami-
no)-1H-pyrrol-2(5H)-one derivatives has been developed by coupling of aldehydes,
amines, and ethyl pyruvate in ethanol promoted by 1-butyl-1-methylpyrrolidinium
hydrogen sulfate. This protocol is endowed with several advantages such as improved
yield, clean reaction, and simple purification.
Experimental
All reagents were purchased from Merck and Aldrich and used without further
purification. All yields refer to isolated products after purification. Nuclear magnetic
resonance (NMR) spectra were recorded on a Bruker Avance DPX 400 MHz
123

Preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives
H
N
N
Ar'
Ar
Ar
ArNH2 + Ar'CHO
a
O
O
O
H
OEt
H
N
ArNH2
+
Ar
OEt
OEt
O
b
c
O
O
H
N
N
Ar
OEt
Ar'
Ar
OEt
Ar'
H
a + c
NH
NH
Ar
e
Ar
d
Ar
O
N
Ar
Ar'
N
H
Scheme 3 Proposed mechanism for preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones
Table 3 Comparison results of 1-butyl-1-methylpyrrolidinium hydrogen sulfate with other catalysts
reported in the literature
Entry Catalyst
Condition
Yield
(%)a
Reference
1
2
3
4
5
6
7
8
Et3NHHSO4
n-Hexane; r.t.; 120 min
Toluene; r.t.; 18 h
Toluene; r.t.; 18 h
74
84
84
[12]
Thiourea
[10]
Phosphoric acid
SiO2–FeCl3
Al(H2PO4)3
Mg(HSO4)2
SiO2–H2SO4
[10]
Solvent-free; r.t. (40 min) to 100 °C (20 min) 70
[11]
EtOH; r.t.; 120 min
EtOH; r.t.; 120 min
EtOH; r.t.; 120 min
EtOH; r.t.; 120 min
25
35
27
89
This work
This work
This work
This work
CH3
N
HSO4
CH3
Isolated yield; based on preparation of 3-(p-tolylamino)-5-phenyl-1-p-tolyl-1H-pyrrol-2(5H)-one
a
instrument. Spectra were measured in CDCl3 relative to tetramethylsilane (TMS,
0.00 ppm). Infrared (IR) spectra were recorded on a PerkinElmer 781 spectropho-
tometer. Elemental analysis was performed on a Heraeus CHN-O-Rapid analyzer.
Melting points were determined in open capillaries with a BUCHI 510 melting point
123

M. Ghashang
apparatus. Thin-layer chromatography (TLC) was performed on silica gel polygram
SIL G/UV 254 plates.
General procedure
To a mixture of aldehyde (1 mmol), aromatic amine (2 mmol), and ethyl pyruvate
(1.5 mmol) in ethanol (5 mL), 1-butyl-1-methylpyrrolidinium hydrogen sulfate
(1 mmol) as catalyst was added, and the mixture was stirred for appropriate time at
ambient condition. Progress of the reaction was monitored by TLC. After
completion of the reaction, the mixture was displaced to a filter paper and washed
with diethyl ether to afford the pure product (Table 2, products a–r).
Selected data
3-(m-Tolylamino)-5-phenyl-1-m-tolyl-1H-pyrrol-2(5H)-one (product d)
1H NMR (400 MHz, CDCl3): 2.29 (s, 3H), 2.36 (s, 3H), 5.69 (d, J = 2.3 Hz, 1H),
6.08 (d, J = 2.3 Hz, 1H), 6.31 (s, 1H), 6.51 (d, J = 8.6 Hz, 1H), 6.69 (s, 1H), 6.93
(d, J = 8.6 Hz, 1H), 7.01 (t, J = 8.3 Hz, 1H), 7.14–7.28 (m, 7H), 7.53-7.59 (m, 2H)
13C NMR (100 MHz, CDCl3): d = 20.8, 21.2, 64.5, 105.3, 108.2, 112.8, 116.3,
121.4, 124.9, 126.9, 127.3, 127.7, 128.7, 129.3, 129.7, 138.7, 139.0, 139.2, 139.5,
143.4, 144.6, 166.6 ppm; IR (KBr): 3316, 3014, 2954, 1674, 1589, 1164, 887, 751,
and 728 cm-1; Found: C, 81.45; H, 6.38; N, 7.99 C24H22N2O; requires: C, 81.33; H,
6.26; N, 7.90 %.
3-(4-Chlorophenylamino)-1-(4-chlorophenyl)-5-(4-methoxyphenyl)-1H-pyrrol-
2(5H)-one (product f)
1H NMR (400 MHz, CDCl3): 3.79 (s, 3H), 5.63 (d, J = 2.5 Hz, 1H), 6.06 (d,
J = 2.5 Hz, 1H), 6.69 (s, 1H), 6.84 (d, J = 8.6 Hz, 2H), 7.02 (d, J = 8.6 Hz, 2H),
7.25–7.31 (m, 6H), 7.54 (d, J = 8.7 Hz, 2H); 13C NMR (100 MHz, CDCl3):
d = 55.4, 63.9, 108.4, 114.9, 117.0, 121.7, 126.1, 128.1, 129.0, 129.2, 131.5, 134.6,
136.8, 140.0, 151.6, 158.5, 167.5 ppm; IR (KBr): 3319, 1673, 1648, 1597, 1524,
1490, 1169, 1014, 824, and 775 cm-1; Found: C, 65.07; H, 4.38; N, 6.67
C23H18Cl2N2O2; requires: C, 64.95; H, 4.27; N, 6.59 %.
3-(4-Chlorophenylamino)-1-(4-chlorophenyl)-5-p-tolyl-1H-pyrrol-2(5H)-one
(product g)
1H NMR (400 MHz, CDCl3): 2.31 (s, 3H), 5.63 (d, J = 2.5 Hz, 1H), 6.04 (d,
J = 2.5 Hz, 1H), 6.69 (s, 1H), 7.01 (d, J = 8.8 Hz, 2H), 7.12 (d, J = 8.4 Hz, 2H),
7.25–7.26 (m, 4H), 7.32 (d, J = 8.0 Hz, 2H), 7.54 (d, J = 8.8 Hz, 2H); 13C NMR
(100 MHz, CDCl3): d = 21.4, 63.5, 108.7, 116.7, 119.6, 122.5, 125.8, 126.5, 129.1,
129.4, 130.0, 131.5, 133.8, 136.7, 139.9, 151.7, 167.4 ppm; IR (KBr): 3319, 1674,
1653, 1597, 1524, 1490, 1169, 1092, 817, and 775 cm-1; Found: C, 67.62; H, 4.55;
N, 6.95 C23H18Cl2N2O; requires: C, 67.49; H, 4.43; N, 6.84 %.
123

Preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives
3-(4-Chlorophenylamino)-5-(4-tert-butylphenyl)-1-(4-chlorophenyl)-1H-pyrrol-
2(5H)-one (product h)
m.p.: 235–237 °C, 1H NMR (400 MHz, CDCl3): 1.30 (s, 9H), 5.65 (d, J = 2.4 Hz,
1H), 6.06 (d, J = 2.4 Hz, 1H), 6.70 (s, 1H), 7.01 (d, J = 8.8 Hz, 2H), 7.13 (d,
J = 8.4 Hz, 2H), 7.25–7.27 (m, 4H), 7.33 (d, J = 8.0 Hz, 2H), 7.56 (d, J = 8.8 Hz,
2H); 13C NMR (100 MHz, CDCl3): d = 31.3, 34.6, 63.8, 108.9, 117.9, 122.4,
126.1, 126.2, 126.3, 129.0, 129.3, 130.1, 131.6, 133.6, 135.9, 139.8, 151.5, and
167.1 ppm; IR (KBr): 3320, 3065, 2965, 2927, 2867, 1670, 1650, 1599, 1541, 1495,
1419, 1393, 1318, 1297, 1268, 1164, 1092, 1015, 919, 870, 833, 819, 796, and
778 cm-1; Found: C, 69.25; H, 5.41; N, 6.27 C26H24Cl2N2O; requires: C, 69.18; H,
5.36; N, 6.21 %.
3-(4-Chlorophenylamino)-1-(4-chlorophenyl)-5-(3,4,5-trimethoxyphenyl)-1H-
pyrrol-2(5H)-one (product i)
1H NMR (400 MHz, CDCl3): 3.77 (s, 6H), 3.79 (s, 3H), 5.66 (d, J = 2.5 Hz, 1H),
6.09 (d, J = 2.5 Hz, 1H), 6.37 (s, 2H), 6.70 (s, 1H), 7.26-7.32 (m, 6H), 7.55 (d,
J = 8.6 Hz, 2H); 13C NMR (100 MHz, CDCl3): d = 55.4, 56.2, 64.2, 104.0, 108.5,
115.2, 117.1, 121.5, 126.3, 128.2, 129.0, 129.5, 131.7, 140.0, 151.6, 154.4, 157.2,
and 167.6 ppm; IR (KBr): 3321, 1677, 1645, 1596, 1524, 1168, 1014, 824, and
776 cm-1; Found: C, 61.99; H, 4.67; N, 5.89 C25H22Cl2N2O4; requires: C, 61.87; H,
4.57; N, 5.77 %.
3-(p-Tolylamino)-5-(3,4,5-trimethoxyphenyl)-1-p-tolyl-1H-pyrrol-2(5H)-one
(product q)
1H NMR (400 MHz, CDCl3): 2.23 (s, 3H), 2.27 (s, 3H), 3.76 (s, 6H), 3.79 (s, 3H),
5.58 (d, J = 2.4 Hz, 1H), 6.05 (d, J = 2.4 Hz, 1H), 6.36 (s, 2H), 6.66 (s, 1H), 7.02
(d, J = 8.5 Hz, 2H), 7.18 (d, J = 8.1 Hz, 2H), 7.23–7.28 (m, 4H) 13C NMR
(100 MHz, CDCl3): d = 21.1, 21.4, 55.4, 55.5, 65.1, 103.9, 106.6, 116.9, 126.0,
129.7, 129.9, 131.0, 133.4, 133.8, 136.9, 137.8, 138.5, 154.4, 157.2, and 168.4 ppm;
IR (KBr): 3319, 3021, 2940, 1675, 1650, 1610, 1543, 1454, 1322, 1185, 1123, 831,
774, and 740 cm-1; Found: C, 73.09; H, 6.46; N, 6.39 C27H28N2O4; requires: C,
72.95; H, 6.35; N, 6.30 %.
3-(m-Tolylamino)-1-m-tolyl-5-p-tolyl-1H-pyrrol-2(5H)-one (product r)
1H NMR (400 MHz, CDCl3): 2.23 (s, 3H), 2.29 (s, 3H), 2.35 (s, 3H), 5.67 (d,
J = 2.4 Hz, 1H), 6.09 (d, J = 2.4 Hz, 1H), 6.30 (s, 1H), 6.49 (d, J = 8.2 Hz, 1H),
6.68 (s, 1H), 6.91 (d, J = 8.2 Hz, 1H), 7.02 (t, J = 8.4 Hz, 1H), 7.10–7.28 (m, 6H),
7.51–7.57 (m, 2H) 13C NMR (100 MHz, CDCl3): d = 20.9, 21.4, 21.6, 63.7, 105.7,
108.5, 113.0, 116.1, 118.9, 119.2, 121.5, 126.8, 127.1, 129.0, 129.6, 136.5, 138.9,
139.2, 139.4, 140.7, 144.4, 144.7, and 167.5 ppm; IR (KBr): 3318, 3021, 2849,
1671, 1602, 1563, 1171, 1052, and 749 cm-1; Found: C, 81.58; H, 6.71; N, 7.71
C25H24N2O; requires: C, 81.49; H, 6.57; N, 7.60 %.
123

M. Ghashang
3-(m-Tolylamino)-5-(3,4,5-trimethoxyphenyl)-1-m-tolyl-1H-pyrrol-2(5H)-one
(product s)
1H NMR (400 MHz, CDCl3): 2.31 (s, 3H), 2.39 (s, 3H), 3.75 (s, 6H), 3.77 (s, 3H),
5.51 (d, J = 2.3 Hz, 1H), 6.02 (d, J = 2.3 Hz, 1H), 6.35 (s, 2H), 6.42 (s, 1H), 6.50
(d, J = 8.3 Hz, 1H), 6.69 (s, 1H), 6.93 (d, J = 8.3 Hz, 1H), 7.05 (t, J = 8.5 Hz,
1H), 7.12–7.26 (m, 2H), 7.50 (d, J = 8.4 Hz, 1H), 7.55 (s, 1H) 13C NMR
(100 MHz, CDCl3): d = 21.1, 21.4, 55.4, 55.5, 65.1, 103.9, 106.0, 108.6, 112.9,
116.2, 119.0, 121.5, 126.8, 127.1, 128.8, 129.0, 129.6, 138.8, 139.2, 140.3, 144.4,
154.4, 157.2, and 167.4 ppm; IR (KBr): 3315, 3019, 2941, 1677, 1649, 1612, 1541,
1455, 1322, 1186, 1125, 832, 775, and 742 cm-1; Found: C, 73.07; H, 6.44; N, 6.38
C27H28N2O4; requires: C, 72.95; H, 6.35; N, 6.30 %.
3-(p-Tolylamino)-5-(furan-2-yl)-1-p-tolyl-1H-pyrrol-2(5H)-one (product t)
1H NMR (400 MHz, CDCl3): 2.35 (s, 6H), 5.78 (d, J = 2.4 Hz, 1H), 6.04 (d,
J = 2.4 Hz, 1H), 6.21 (d, J = 2.8 Hz, 1H), 6.28 (s, 1H), 6.65 (s, 1H), 7.04 (d,
J = 8.0 Hz, 2H), 7.15–7.19 (m, 4H), 7.33 (s, 1H), 7.37 (d, J = 8.4 Hz, 2H); 13C
NMR (100 MHz, CDCl3): d = 20.7, 21.0, 58.1, 102.9, 108.4, 110.5, 116.9, 122.6,
129.6, 129.9, 130.8, 133.5, 134.4, 135.3, 138.8, 142.6, 150.1, and 166.7 ppm; IR
(KBr): 3314, 3032, 2920, 2856, 1679, 1650, 1616, 1590, 1572, 1543, 1515, 1461,
1422, 1401, 1323, 1304, 1276, 1238, 1212, 1165, 1150, 1101, 1071, 929, 883, 867,
849, 821, 800, and 777 cm-1; Found: C, 76.82; H, 5.93; N, 8.17 C22H20N2O2;
requires: C, 76.72; H, 5.85; N, 8.13 %.
3-(4-Methoxyphenylamino)-5-(furan-2-yl)-1-(4-methoxyphenyl)-1H-pyrrol-2(5H)-
one (product w)
1H NMR (400 MHz, CDCl3): 3.73 (s, 3H), 3.77 (s, 3H), 5.76 (d, J = 2.6 Hz, 1H),
6.05 (d, J = 2.6 Hz, 1H), 6.21 (d, J = 3.0 Hz, 1H), 6.28 (d, J = 3.0 Hz, 1H), 6.65
(s, 1H), 6.89 (d, J = 8.4 Hz, 2H), 7.03 (d, J = 8.4 Hz, 2H), 7.11 (d, J = 8.6 Hz,
2H), 7.28–7.34 (m, 3H); 13C NMR (100 MHz, CDCl3): d = 55.3, 55.8, 60.1, 103.1,
105.9, 110.6, 114.8, 118.5, 124.6, 129.6, 129.9, 133.6, 135.3, 142.6, 150.2, 154.9,
157.2, and 166.9 ppm; IR (KBr): 3321, 3031, 2925, 1675, 1651, 1614, 1591, 1541,
1462, 1275, 1234, 1210, 1163, 1103, 1070, 881, 866, 823, and 776 cm-1; Found: C,
70.31; H, 5.47; N, 7.53 C22H20N2O4; requires: C, 70.20; H, 5.36; N, 7.44 %.
Acknowledgments The authors are indebted to the Islamic Azad University, Najafabad Branch for
financial support of this research.
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