An efficient catalyst-free one-pot synthesis of primary amides from the aldehydes of the Baylis-Hillman reaction

Article abstract of DOI:10.1039/c7nj01965c

Herein, a facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis-Hillman adducts has been developed using a hydroxylamine/methanol system under a catalyst-free condition. The effects of solvents and temperature on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its advantages such as operational simplicity, moderate to excellent yields, short reaction time, and simple reaction procedure. Most importantly, the reaction proceeds smoothly in the absence of a catalyst and an external oxidant.

Full text of DOI:10.1039/c7nj01965c

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PAPER
Jason B. Benedict et al.
The role of atropisomers on the photo-reactivity and fatigue of
diarylethene-based metal–organic frameworks
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An efficient catalyst-free one-pot synthesis of primary amides
from aldehydes of Baylis-Hillman Reaction
Thatikonda Narendar Reddy,*ab Raktani Bikshapathi,ab Perla Ramesh,c Mettu Ravinder,ab Vaidya
Jayathirtha Rao,*ab and N. Jagadeesh Babud
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
A facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis-Hillman adducts has been
developed using hydroxylamine/methanol system under catalyst-free condition. The effect of solvents, temperature effect
on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its
advantages like operational simplicity, moderate to excellent yields, short reaction time and simple reaction procedure.
Most importantly, the reaction proceeds smoothly in the absence of a catalyst and external oxidant.
www.rsc.org/
imperative intermediates in the synthesis of amides.8
However, the applications of these existing methods are still
inadequate due to some flaws, such as harsh reaction
Introduction
The amide is
a ubiquitous functionality of numerous
conditions, poor atom-efficiency, longer reaction time, use of
hazardous reagents, tedious workup, and generation of
wastes.
biologically active molecules and forms an essential integral
part of many natural products, functional materials and
pharmaceutical drugs (Fig. 1).1 These are significant
intermediates in the modern organic synthesis and used as
raw materials for engineering plastics, detergent
manufacturing, pesticides, lubricants, anti-block reagents,
intensifiers of perfume, natural products, proteins, peptides,
bio-molecules and materials science.2 Furthermore, the
important advantage properties of amides, such as good
stability, high polarity and conformational diversity, make it
one of the most reliable and popular functional groups in
organic chemistry. Particularly, α,β-unsaturated primary
amides are synthetically important key intermediates and
useful precursors for various biologically active compounds
and pharmaceuticals.3-5
Fig. 1 Amide bond in pharmaceutical drugs.
To overcome these problems, numerous synthetic approaches
have been reported such as Beckmann rearrangement,9
Traditionally, the most common and basic methodology for
the synthesis of the primary amide is ammonolysis of
carboxylic acid derivatives such as acids, acyl halides,
anhydrides and esters.6 Another attractive method for the
preparation of amide is the amino carbonylation of olefins in
the presence of transition metal catalysts.7 Carbonyl
compounds such as aldehydes, ketones, and oximes are
Staudinger reaction,10 Aube-Schmidt reaction,11
amino
carbonylation of haloarenes,12 iodonium-promoted α-
bromonitroalkane with amine coupling,13 direct amide from
alcohols with nitroarenes or amines,14 hydroamination of
alkynes,15 amidation of thioacids in the presence of azides,16
from primary amides by transamidation,17 from organonitriles
by hydration18 and N-formylation of amines by aerobic
oxidation.19 Importantly, oxidative amidation of aldehydes via
C-H activation of aldehyde is one of the elegant approaches
that have been used as less hazardous than those traditional
methods.20 Several methods for oxidative amidation of
aldehydes with amines have been reported using
stoichiometric amounts of oxidant/catalyst such as NBS,21
iodine,22 tert-butyl hydroperoxide (TBHP),23 3,3,5,5-tetra-tert-
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butyldiphenoquinone,24 N-heterocyclic carbene (NHC),25 temperature, using model substrate 4a. Different polar and
lanthanides26 and transition metals.27 In fact, to the best of our non-polar solvents were used for standardization of the
knowledge, there are few methodologies explored for the reaction conditions and the best results were realized in
direct conversion of aldehydes into primary amides using methanol/ethanol system (Table 1, entries 2 and 3). Notably,
NH2OH.HCl in the presence of catalyst.28
the reaction was smoothly performed in both methanol and
In above cases, significant results were obtained but the use of ethanol underwent effortlessly and no change in the yield as
expensive metal catalysts and utilisation of other co-reagents wells as the time of the reaction at reflux temperature (Table
were restricted for large scale reactions. Therefore, the 1, entry 4 and 5).
development of a simple, efficient and promising method to
access primary amides remains highly desirable. In this
context, the novel and practical methods for the synthesis of
primary amide, whether catalyst-free or waste-free are in
great demand.
In recent years, the Baylis-Hillman reaction has attracted the
attention of many organic chemists, because it is a simple,
straightforward method for the generation of attractive
densely functional molecules.29 During the past few years, a lot
of our efforts have been devoted to Baylis-Hillman chemistry
and its applications towards the synthesis of new heterocyclic
compounds.30 Some of our synthesized compounds even
displayed good biological activity.31
Our research into new methodologies for environmentally
benign processes32 prompted us to investigate the direct
Scheme 1 Synthesis of amides.
transformation of cyanocinnamaldehydes into primary amides.
Herein, we described the use of hydroxylamine as an excellent
Table 1 Optimization of the reaction conditionsa
reagent for the easy and mild adaptation of Baylis–Hillman
adducts into the corresponding allyl amides under a catalyst-
free condition in methanol. This reaction is fast, smooth, clean
and high yielding.
Entry Solvent (Temp)
Time (h) Yield (%)b
Results and discussion
1
2
3
4
5
6
MeOH (rt)
MeOH (rt)
EtOH (rt)
MeOH (reflux)
EtOH (reflux)
MeOH/EtOH
(4 Å MS, reflux)
Aq. MeOH
5
5
5
2
2
2
30c
49
50
84
84
-
The synthesis of substituted (E)-2-cyano-3-phenylacrylamide
( -s) as outlined in Scheme 1 commenced with the Baylis-
5a
Hillman (BH) reaction of a series of substituted aromatic
aldehydes (1a-s) with acrylonitrile ( ) using a catalytic amount
of DABCO at room temperature under solvent-free
condition.31c The synthesized Baylis-Hillman adducts (3a-s
were converted into corresponding substituted (E)-α-
cyanocinnamaldehydes 4a-s using the well know
procedure.31c,33 At this stage, our initial attempt was made to
synthesis of 2,3-dihydroisoxazoles from (E)-α-
2
)
7
24
24
24
24
24
24
24
24
-
-
-
-
-
-
40
30
8
CH3CN (rt)
(
)
9
Toluene (rt)
AcOH (rt)
DCM (rt)
THF (rt)
AcOH (reflux)
Toluene (reflux)
10
11
12
13
14
cyanocinnamaldehydes using NH2OH.HCl. However, to our
surprise, an unexpected cinnamylamide (5a) was obtained in
30% yield instead of 2,3-dihydroisoxazole when the reaction
was carried out in the presence of 1 equivalent NH2OH.HCl in
methanol at room temperature using 4a as a substrate (Table
1, entry 1). Pleasingly, reaction yield could be increased up to
49% with 2 equivalents of NH2OH.HCl (Table 1, entry 2). It
aReaction conditions: 4a (0.4 mmol), NH2OH.HCl (2 equiv),
solvent (2 mL). bIsolated yields. cNH2OH.HCl (1 equiv).
No amide could be obtained when the reaction was performed
in methanol or ethanol using molecular sieves under identical
conditions (Table 1, entry 6). Importantly, when aqueous
methanol was used as a solvent the desired product 5a was
not obtained (Table 1, entry 7). It was noticed that the reaction
was not initiated with some organic solvents such as CH3CN,
could be found that the amount of NH2OH.HCl had
a
noteworthy influence on the formation of the product 5a. In
this sense, to improve the yield of the reaction, we started our
investigations by testing various solvent systems with 2
equivalents of NH2OH.HCl at room temperature or reflux
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toluene, acetic acid, DCM and THF at room temperature (Table yields as listed in Table 2. Therefore, phenyl group containing
1, entries 8-12). However, when the reaction was carried out the electron-donating as well as withdrawing groups at
at reflux temperature in acetic acid or toluene the desired different positions have been employed efficiently in this
product 5a was obtained in lower yields (entry 13 and 14). protocol irrespective of the steric and electronic character of a
From Table 1, it could also be found that the reaction was substituent on the phenyl ring. To our delight, this method
indolent at room temperature and absolute conversion could could also be applied to the transformation of hetero-atom
be occurred at reflux temperature within short period of time containing cinnamaldehydes, such as 2-furyl, 2-thienyl, 3-
(2 h) when the reaction was carried out in methanol.
Having optimized reaction conditions in hand, to further probe such as naphthyl cinnamaldehyde could be tolerated well
the scope and limitations of this method variety of under the optimal conditions, and smoothly afforded the
thienyl and 5-bromo-2-thienyl as well as extended aromatics,
a
substituted cinnamaldehydes could be effectively renewed corresponding amides, in good yields.
into the corresponding amides (5a-s) in good to excellent
Table 2 Direct synthesis of primary amides from aldehydes under catalyst-free conditiona
Time Yield
(%)b
Time Yield
(%)b
Entry
Aldehyde
Amide
Entry
Aldehyde
Amide
(h)
(h)
CHO
1
2
87
11
2
81
CN
Br
4k
CHO
CN
2
2.8
77
12
2
76
4l
Br
3
4
5
2.5
2.5
3
75
77
76
13
14
15
2
2
2
82
76
74
6
7
3
81
82
16
17
2.5
3
84
78
2.5
8
3
85
18
19
3
81
85
9
2.6
2
85
78
2.5
10
aThe reaction was conducted with
4 (1 mmol) and NH2OH.HCl (2 mmol) in 5 mL of methanol at reflux temperature.
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bIsolated yield.
On the other hand, to further investigate the practical
application of this alteration in organic synthesis, the gram-
scale reaction of 4a was performed under standard reaction
conditions. Interestingly, compound 5a was smoothly afforded
in 90% yield without any decrease when compared to the
small-scale reaction (Table 2, entry 1). The cyanoacrylamide
scaffolds play significant role in the field of synthetic organic
chemistry and medicinal community, and they also possess
fluorescent properties.34
The spectral data (1H NMR, 13C NMR, Mass, and IR) of the
synthesized compounds are in full agreement with proposed
structures. The 1H NMR of spectra of the compound 5a
showed two broad singlets at 6.34 and 5.94 ppm
corresponding to exchangeable amide (NH2) hydrogens.
Further, signals of the corresponding aromatic and aliphatic
protons were present as well. The 13C NMR spectra exhibited
signal at 115 ppm corresponding to the nitrile group, the signal
appeared at downfield region 160 ppm corresponding to the
amide group (C=O). In addition, IR spectra of products showed
a signal at 2220 cm-1, due to the presence of nitrile group and
signal at 1690 cm-1 corresponding to the carbonyl amide (NH2)
group. Furthermore, the structure of compound 5a was fully
established by a single crystal X-ray diffraction analysis (Fig. 2).
Conclusions
In this paper, we disclosed a novel, efficient and useful
pathway for the synthesis of primary amide derivatives under
simple reaction conditions. Baylis-Hillman adducts were used
in the synthesis of new amide derivatives and characterized by
spectral analyses. Application of this strategy to the
preparation of new heterocyclic entities from allyl amides is
currently being pursued. Moreover, this pathway has
advantages like oxidant-free and catalyst-free conditions as
well. Further studies on the mechanism and synthetic
applications are ongoing in our research group.
Experimental section
General
All commercially available chemicals were used without
further purification. Melting points were determined on a Mel-
Temp apparatus and are uncorrected. IR spectra were
recorded using
a
Thermo Nicolet Nexus 670 FTIR
spectrometer. The NMR spectra were recorded on Bruker
1
Avance 300 spectrometer at 300 MHz for H and 75 MHz for
13C, respectively, using TMS as an internal standard. The
chemical shifts are expressed as δ values in parts per million
(ppm) and the coupling constants (J) are given in Hertz (Hz).
ESI-MS was obtained on Thermo-Finnigan MAT-1020B
instrument. Column chromatography was performed on silica
gel (60-120 mesh, Acme, India).
General procedure for the synthesis of Baylis-Hillman adducts
(3a-s)31c
Aromatic aldehydes (1a-s) (5 mmol), acrylonitrile (2) (10 mmol)
and DABCO (30 mol% with respect to aldehyde) were mixed
and allowed to stir at room temperature until completion of
the reaction (10-12 h) was monitored by TLC. After that, the
reaction mixture was diluted with water (15 mL) and extracted
with ethyl acetate (3 × 25 mL). The combined organic layers
were dried over Na2SO4, concentrated under reduced pressure
and purified by column chromatography using 10% EtOAc in
Fig. 2 ORTEP diagram of compound 5a with the atom-
numbering. Displacement ellipsoids are drawn at the 30%
probability level and H atoms are shown as small spheres of
arbitrary radius.
NOH
N
NH2OH.HCl
CHO
hexane as eluent to afford pure Baylis-Hillman adducts (3a-s
)
+
Ph
Ph
Ph
MeOH, reflux, 3 h
in 80-90% yield. The spectroscopic and analytical data of all the
synthesized compounds were in good agreement with those
reported in the literature.31c,29
6
7
8
OH
NH2OH.HCl
N
O
General procedure for the synthesis of [E]-
α-
MeOH, reflux, 3 h
9
10
cyanocinnamaldehyde (4a-s)
Scheme 2
A stirred solution of BH adduct 3a-s (1 mmol) and NaNO3 (1
o
mmol) in 1 mL of [Hmim]HSO4 was heated at 80 C for 1–2 h.
The reaction progress was monitored by TLC. Upon
completion, the reaction mixture was cooled to room
temperature and extracted with ethyl acetate (3 × 15 mL). The
combined organic layers were dried over Na2SO4, filtered and
evaporated under reduced pressure. The resulting crude
product was purified by column chromatography using 10%
We also tried to use simple aldehydes such as trans-
cinnamaldehyde and benzaldehyde. The reaction of trans-
cinnamaldehyde (
conditions gave a mixture of oxime (
ratio respectively. On the other hand, the benzaldehyde (
6
) with NH2OH.HCl under optimal reaction
7
) and nitrile ( ) with 9:1
8
9)
provided oxime (10) as the only product in 94% yield (Scheme
2).
EtOAc in hexane as eluent to afford pure [E]-α-
cyanocinnamaldehyde derivatives (4a-s). The characterization
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1
data of the newly synthesized compounds were given White solid; Yield: 76%; mp: 145-146 oC; H NMR (300 MHz,
below.31c,33
CDCl3): δ 8.31 (s, 1H), 7.77 (d, J = 7.4 Hz, 1H), 7.74 (s, 1H), 7.42-
7.35 (m, 2H), 6.36 (brs, 1H), 5.97 (brs, 1H), 2.42 (s, 3H); 13C
(E)-2-Formyl-3-(3-methoxyphenyl)acrylonitrile (4h)
White solid; Yield: 71%; mp: 80-83 oC; 1H NMR (300 MHz, NMR (75 MHz, CDCl3+DMSO-d6): δ 161.2, 149.3, 137.8, 130.6,
CDCl3): δ 9.57 (s, 1H), 7.83 (s, 1H), 7.69-7.67 (m, 1H), 7.50-7.40 130.0, 129.6, 126.8, 125.1, 115.3, 106.3, 18.5; IR (KBr, cm-1):
(m, 2H), 7.16-7.12 (m, 1H), 3.89 (s, 3H); ESI-MS (m/z) 188 3492, 3384, 3182, 2920, 2223, 1694, 1594, 1391, 1300, 1245;
[M+H]+.
MS (ESI) m/z (%): 187 [M+H]+.
(E)-3-(3-Chlorophenyl)-2-formylacrylonitrile (4m)
(E)-2-Cyano-3-o-tolylacrylamide (5f)
White solid; Yield: 62%; mp: 92-94 oC; 1H NMR (300 MHz, White solid; Yield: 81%; mp: 139-140 oC; H NMR (300 MHz,
CDCl3): δ 9.60 (s, 1H), 8.00-7.95 (m, 2H), 7.85 (s, 1H), 7.60 (d, J CDCl3): δ 8.66 (s, 1H), 8.07 (d, J = 7.5 Hz, 1H), 7.46-7.39 (m,
= 7.7 Hz, 1H), 7.51 (t, J = 7.7 Hz, 1H). ESI-MS (m/z) 209 1H), 7.36-7.28 (m, 2H), 6.38 (brs, 1H), 6.02 (brs, 1H), 2.46 (s,
1
[M+NH4]+.
3H); 13C NMR (75 MHz, CDCl3+DMSO-d6): δ 161.7, 149.9, 138.4,
General procedure for the synthesis of (E)-2-cyano-3- 131.2, 130.6, 130.2, 127.4, 125.7, 115.9, 106.8, 19.1; IR (KBr,
phenylacrylamide (5a-s)
cm-1): 3410, 3313, 3170, 2924, 2221, 1699, 1594, 1480, 1382,
α
-cinnamaldehyde 1293, 1225; MS (ESI) m/z (%): 187 [M+H]+.
4a-s (1 mmol) in methanol (5 mL) was added hydroxylamine (E)-2-Cyano-3-(4-methoxyphenyl)acrylamide (5g)
To a magnetically stirred suspension of (E)-
1
hydrochloride (2 mmol) in one portion and stir the reaction White solid; Yield: 82%; mp: 210-212 oC; H NMR (300 MHz,
mixture under reflux for the appropriate time, the reaction CDCl3+DMSO-d6): δ 8.26 (s, 1H), 7.97 (d, J = 8.8 Hz, 2H), 7.00 (d,
evolution was monitored by TLC. Upon completion, the J = 8.8 Hz, 2H), 6.28 (brs, 1H), 5.68 (brs, 1H), 3.98 (s, 3H); 13C
reaction mixture was cooled to room temperature and solvent NMR (75 MHz, CDCl3+DMSO-d6): δ 161.3, 161.0, 148.8, 130.8,
was removed under reduced pressure. The resulting crude 122.8, 115.4, 112.9, 100.8, 53.8; IR (KBr, cm-1): 3445, 3303,
product was purified by column chromatography to afford 3170, 2927, 2205, 1697, 1582, 1508, 1386, 1361, 1260, 1176;
pure [E]-α
-acrylamide (5a-5s) as white solid. Other amide MS (ESI) m/z (%): 203 [M+H]+.
derivatives were prepared in a similar way. All compounds (E)-2-Cyano-3-(3-methoxyphenyl)acrylamide (5h)
1
were characterised by 1H NMR, 13C NMR, IR and Mass and White solid; Yield: 85%; mp: 145-147 oC; H NMR (300 MHz,
compared with the reported data.34
CDCl3): δ 8.31 (s, 1H), 7.52 (m, 1H), 7.51-7.49 (m, 1H), 7.41 (t, J
(E)-2-Cyano-3-phenylacrylamide (5a)
= 8.0 Hz, 1H), 7.12-7.09 (m, 1H), 6.34 (brs, 1H), 5.92 (brs, 1H),
White solid; Yield: 87%; mp: 115-116 oC; H NMR (300 MHz, 3.86 (s, 3H); 13C NMR (75 MHz, CDCl3+DMSO-d6): δ 162.1,
CDCl3): δ 8.34 (s, 1H), 7.98-7.93 (m, 2H), 7.59-7.47 (m, 3H), 159.1, 150.4, 132.7, 129.6, 122.5, 117.8, 116.0, 114.1, 106.0,
6.39 (m, 2H); 13C NMR (75 MHz, CDCl3): δ 162.2, 153.9, 132.9, 54.8; IR (KBr, cm-1): 3394, 3312, 3176, 2997, 2222, 1717, 1672,
131.5, 130.7, 129.1, 116.9, 103.1; MS (ESI) m/z (%): 173 1597, 1487, 1461, 1378, 1259; MS (ESI) m/z (%): 203 [M+H]+.
1
[M+H]+.
(E)-2-Cyano-3-(2-methoxyphenyl)acrylamide (5i)
1
(E)-2-Cyano-3-(4-ethylphenyl)acrylamide (5b)
White solid; Yield: 85%; mp: 132-134 oC; H NMR (300 MHz,
White solid; Yield: 77%; mp: 129-130 oC; H NMR (300 MHz, CDCl3): δ 8.81 (s, 1H), 8.18 (dd, J = 7.7, 1.5 Hz, 1H) 7.53-7.49
CDCl3): δ 8.31 (s, 1H), 7.90 (d, J = 8.3 Hz, 2H), 7.33 (d, J = 8.3 (m, 1H), 7.05 (t, J = 7.4 Hz, 1H), 6.96 (d, J = 7.7 Hz, 1H), 6.34
Hz, 2H), 6.34 (brs, 1H), 5.94 (brs, 1H), 2.76-2.69 (q, J = 7.5 Hz, (brs, 1H), 6.01 (brs, 1H), 3.90 (s, 3H); 13C NMR (75 MHz,
2H), 1.27 (t, J = 7.5 Hz, 3H); 13C NMR (75 MHz, CDCl3): δ 162.4, CDCl3+DMSO-d6): δ 162.1, 158.1, 145.9, 133.5, 128.0, 120.3,
153.8, 150.4, 131.0, 129.1, 128.7, 117.2, 101.6, 29.0, 14.9; IR 120.1, 116.3, 110.9, 104.9, 55.2; IR (KBr, cm-1): 3399, 3261,
(KBr, cm-1): 3378, 3314, 3166, 2967, 2932, 2220, 1694, 1586, 3207, 3001, 2934, 2208, 1667, 1578, 1489, 1461, 1379, 1303,
1
1507, 1370, 1212, 1180; MS (ESI) m/z (%): 201 [M+H]+.
1253, 1161; MS (ESI) m/z (%): 203 [M+H]+.
(E)-2-Cyano-3-(4-isopropylphenyl)acrylamide (5c)
(E)-2-Cyano-3-(4-fluorophenyl)acrylamide (5j)
White solid; Yield: 75%; mp: 112-114 oC; 1H NMR (300 MHz, White solid; Yield: 78%; mp: 147-149 oC; H NMR (300 MHz,
CDCl3): δ 8.31 (s, 1H), 7.90 (d, J = 8.3 Hz, 2H), 7.36 (d, J = 8.3 CDCl3): δ 8.31 (s, 1H), 8.02-7.96 (m, 2H), 7.20 (t, J = 8.4 Hz, 2H),
Hz, 2H), 6.36 (brs, 1H), 6.06 (brs, 1H), 3.05-2.91 (m, 1H), 1.28 6.33 (brs, 1H), 5.86 (brs, 1H); 13C NMR (75 MHz, CDCl3+DMSO-
(d, J = 6.7 Hz, 6H); 13C NMR (75 MHz, CDCl3+DMSO-d6): δ 162.6, d6): δ 165.8, 162.4, 161.7, 150.2, 132.4 (d), 127.7, 116.1, 115.9
153.2, 150.2, 130.1, 129.4, 126.9, 116.4, 105.1, 33.4, 23.2; IR (d), 104.0; IR (KBr, cm-1): 3468, 3367, 3303, 3164, 2213, 1700,
(KBr, cm-1): 3417, 3202, 2958, 2212, 1690, 1590, 1461, 1378, 1587, 1501, 1412, 1234, 1161; MS (ESI) m/z (%): 213 [M+Na]+.
1
1283, 1212; MS (ESI) m/z (%): 215 [M+H]+.
(E)-3-(4-Bromophenyl)-2-cyanoacrylamide (5k)
Pale yellow solid; Yield: 81%; mp: 220-222 oC; 1H NMR (300
(E)-2-Cyano-3-p-tolylacrylamide (5d)
White solid; Yield: 77%; mp: 150-152 oC; 1H NMR (300 MHz, MHz, CDCl3): δ 8.28 (s, 1H), 7.82 (d, J = 8.4 Hz, 2H), 7.65 (d, J =
CDCl3): δ 8.30 (s, 1H), 7.87 (d, J = 7.9 Hz, 2H), 7.31 (d, J = 7.9 8.4 Hz, 2H), 6.33 (brs, 1H), 5.76 (brs, 1H); 13C NMR (75 MHz,
Hz, 2H), 6.34 (brs, 1H), 5.93 (brs, 1H), 2.43 (s, 3H); 13C NMR (75 CDCl3+DMSO-d6): δ 161.8, 149.2, 131.7, 131.2, 130.5, 125.9,
MHz, CDCl3+DMSO-d6): δ 162.4, 150.4, 142.5, 129.9, 129.3, 115.7, 106.3; IR (KBr, cm-1): 3437, 3144, 2924, 2853, 2211,
128.8, 116.3, 104.5, 21.0; IR (KBr, cm-1): 3386, 3156, 2924, 1699, 1599, 1576, 1483, 1397, 1373, 1275; MS (ESI) m/z (%):
2217, 1695, 1590, 1373, 1211, 1180; MS (ESI) m/z (%): 187 252 [M+H]+.
[M+H]+.
(E)-3-(3-Bromophenyl)-2-cyanoacrylamide (5l)
(E)-2-cyano-3-m-tolylacrylamide (5e)
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White solid; Yield: 76%; mp: 136-138 oC; 1H NMR (300 MHz, White solid; Yield: 85%; mp: 191-192 oC; H NMR (300 MHz,
CDCl3): δ 8.27 (s, 1H), 8.03 (s, 1H), 7.91 (d, J = 7.7 Hz, 1H), 7.68 CDCl3): δ 9.20 (s, 1H), 8.24 (d, J = 7.6 Hz, 1H), 8.09 (d, J = 8.2
(d, J = 7.9 Hz, 1H), 7.39 (t, J = 7.9 Hz, 1H), 6.34 (brs, 1H), 5.77 Hz, 1H), 8.04 (d, J = 8.2 Hz, 1H), 7.93 (d, J = 7.6 Hz, 1H), 7.65-
(brs, 1H); 13C NMR (75 MHz, CDCl3+DMSO-d6): δ 161.1, 149.9, 7.58 (m, 3H), 6.40 (brs, 1H), 5.92 (brs, 1H); 13C NMR (75 MHz,
134.5, 133.2, 132.2, 130.1, 128.1, 122.3, 115.6, 105.9; IR (KBr, CDCl3+DMSO-d6): δ 162.2, 148.1, 132.8, 131.5, 130.7, 129.0,
cm-1): 3468, 3371, 2924, 2208, 1690, 1592, 1554, 1468, 1374, 128.4, 127.0, 126.8, 126.3, 125.0, 123.2, 115.7, 110.5; IR (KBr,
1291, 1200; MS (ESI) m/z (%):252 [M+H]+.
cm-1): 3404, 3312, 3169, 2922, 2221, 1696, 1590, 1382, 1351,
1242; MS (ESI) m/z (%): 223 [M+H]+.
(E)-3-(3-Chlorophenyl)-2-cyanoacrylamide (5m)
White solid; Yield: 82%; mp: 131-133 oC; 1H NMR (300 MHz,
CDCl3): δ 8.28 (s, 1H), 7.89 (t, J = 1.8 Hz, 1H), 7.87-7.84 (m, 1H),
7.54-7.51 (m, 1H), 7.45 (t, J = 7.9 Hz, 1H), 6.35 (brs, 1H), 5.82
(brs, 1H); 13C NMR (75 MHz, CDCl3+DMSO-d6): δ 161.6, 148.9,
133.9, 133.3, 131.3, 130.1, 129.0, 127.9, 115.5, 107.2; IR (KBr,
cm-1): 3471, 3331, 3215, 2922, 2210, 1692, 1595, 1563, 1421,
1373, 1204; MS (ESI) m/z (%): 207 [M+H]+.
Acknowledgements
The authors thank the Director, CSIR-Indian Institute of
Chemical Technology for encouragement. VJR thanks, CSIR-
New Delhi for Emeritus Scientist Honour and CSC-0108-ORIGIN
project. TNR and BR acknowledge the CSIR-UGC New Delhi, for
research fellowships.
(E)-3-(2-Chlorophenyl)-2-cyanoacrylamide (5n)
White solid; Yield: 76%; mp: 150-151 oC; 1H NMR (300 MHz,
CDCl3): δ 8.77 (s, 1H), 8.15 (dd, J = 7.7, 1.5 Hz, 1H), 7.52 (dd, J =
8.0, 1.3 Hz, 1H), 7.48 (td, J = 8.0, 1.5 Hz, 1H), 7.41 (td, J = 7.7,
1.3 Hz, 1H), 6.34 (brs, 1H), 5.92 (brs, 1H); 13C NMR (75 MHz,
CDCl3+DMSO-d6): δ 161.2, 146.9, 134.4, 132.4, 130.0, 129.6,
129.0, 126.9, 115.2, 109.4; IR (KBr, cm-1): 3470, 3376, 3148,
2923, 2214, 1707, 1601, 1467, 1437, 1379, 1280, 1208; MS
(ESI) m/z (%):206 [M]+.
Notes and references
1
2
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Light brown solid; Yield: 74%; mp: 140-142 oC; H NMR (300
MHz, CDCl3): δ 8.07 (s, 1H), 7.75 (d, J = 1.5 Hz, 1H), 7.23 (d, J =
3.6 Hz, 1H), 6.65-6.64 (dd, J = 3.6, 1.5 Hz, 1H), 6.29 (brs, 1H),
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3408, 3311, 3203, 2923, 2212, 1696, 1595, 1468, 1380, 1321,
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(E)-2-Cyano-3-(thiophen-2-yl)acrylamide (5p)
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White solid; Yield: 84%; mp: 150-152 oC; H NMR (300 MHz,
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1249, 1160; MS (ESI) m/z (%): 179 [M+H]+.
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