International Journal of Application or Innovation in Engineering & Management (IJAIEM)

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Volume 7, Issue 8, August 2018 ISSN 2319 - 4847

Synthesis, spectral study and properties of Pyridine

chalcone
S.N.Ipper1, N.K.Raut2, P.P.Dixit3 ,G.K.Kakade4

1
Dept. of Chemistry, Sunderrao Solanke Mahavidyalaya, Majalgoan Dist.Beed (India)
2
Dept. of Physics, Sunderrao Solanke Mahavidyalaya, Majalgoan Dist.Beed (India)
3
Department of Microbiology Dr. B.A.M.U.Subcenter Osmanabad(India)
4
Dept. of Chemistry, A.C.S.College, Kille-Dharur Dist.Beed (India)

Abstract
Pyridine chalcone is open chain containing unsaturated carbonyl group consisting of two aromatic rings. Pyridine
chalcone is synthesized by Claisen-Schmidt condensation method in alkaline solution. Spectroscopic characterization using
Electronic absorption, Infra red, 1H NMR spectra and chemical tests has are studied for Pyridine chalcone. Physico-chemical
properties, 1H NMR, IR, Electronic absorption spectra and CHO analysis study of this compound shows that it is novel Pyridine
chalcone.
Keywords: Pyridine chalcone, 1H NMR spectrum, properties, Infra red spectrum, Electronic absorption spectrum, CHO
analysis, Claisen-Schmidt condensation method.

1. Introduction
The chemistry of chalcones has generated intensive scientific studies throughout the world. Especially interest has been
focused on the synthesis and biodynamic activities of chalcones. The chalcone name was firstly given by Kostanecki
and Tambar. The chalcones (1, 3-di-azyl-2-propenones) and their derivatives are important intermediates in organic
synthesis [1]. They serve as starting materials for the synthesis of variety of heterocyclic compounds which are due to
the presence of enone functionality in chalcone moiety confers biological activity upon it, like anti-inflammatory,
antifungal ,antioxidant, antimalarial .Chalcones are open chain containing α, β- unsaturated carbonyl group consisting
of two aromatic rings (ring A & B) having diverse any of substituent’s . In this paper we synthesize Pyridine chalcone
by Claisen-Schmidt condensation method and characterize it by Infra red, Electronic absorption, 1H NMR spectra,
Wilson’s test, FeCl3 test, unsaturation test with KMnO4. Pyridine chalcone is a basic heterocyclic organic compound
with the chemical formula C14H11NO3 [2-3].

2. METHOD
Pyridine chalcone is synthesized by Claisen-Schmidt condensation of pyridine-2-carbalaldehyde and 2, 6-dihydroxy
acetophenone by base catalyzed followed by dehydration. The chemicals used for preparation of Pyridine chalcone are
of A.R. grade. The mixture of 2, 6-dihydroxy acetophenone (0.01 mol) and pyridine-2-carbaldehyde (0.01 mol) are
dissolved in ethyl alcohol (25ml) and then potassium hydroxide 10ml (40%) were added to it. The reaction mixture
was heated for 3 hours till yellowish brown color ppt was obtained [4-6]. The progress of reaction was monitored by
TLC. After completion of reaction the contents were poured into ice water and then acidified by dil. HCl. The solid
obtained was filtered and crude product was recrystallized from ethyl alcohol to give the Pyridine chalcone [7-10]. The
reaction of formation of Pyridine chalcone is given in figure (1). The melting point of the Pyridine chalcone is
determined by an open capillary tube and is unconfirmed. Infra red spectrum is recorded using FT-IR
spectrophotometer, 1H NMR spectrum is recorded on Bruker AVANCE II 400 MHz Spectrophotometer in DMSO
solvent using TMS as an internal standard at SAIF, Chandigarh ,Punjab and Electronic absorption spectrum
measured on SL159, single beam UV-VIS spectrophotometer. The purity of compound is checked by TLC plate, which
were precoated with silica gel using solvent ethyl acetate and petroleum ether (3:7). The IUPAC name of this
compound is (E)-1-(2, 6-dihydroxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one.

3. RESULT AND DISCUSION

3.1 Properties

The Pyridine chalcone having IUPAC name 1-(2, 6-di-hydroxyphenyl)-3-(1 H-pyrrole-2-yl) prop-2-en-1-one were
synthesized by Claisen-Schmidt condensation method and its structure is stable at room temperature, insoluble in water
and is soluble in organic solvent(ethyl alcohol). The stoichiometry of the compound represented as 1:1 pyridine-2-

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International Journal of Application or Innovation in Engineering & Management (IJAIEM)
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Volume 7, Issue 8, August 2018 ISSN 2319 - 4847

carbaldehyde and 2, 6-dihydroxy acetophenone ratio. The physico-chemical properties of Pyridine chalcone are given
in table no. (1) and CHO analysis by calculation method in table no. (2).The completion of reaction was checked by
thin layer chromatography, Wilson’s test, FeCl3 test. The reaction between pyridine-2-carbaldehyde and 2, 6-dihydroxy
acetophenone is shown in figure (1).From the reaction mechanism it is observed that condensation of aldehyde group
of pyridine-2-carbaldehyde and ketone group of 2, 6-dihydroxy acetophenone takes place in the presence of alkali
catalyst.
3.2 Infra red spectrum
In infrared spectrum the sample is exposed to infrared radiation and the wavelength scanned across the spectrum.
Whenever energy corresponding to specific wave length is absorbed, the intensity of the radiation reaching a detector
momentarily decreases, and this is recorded in the spectrum. Infrared spectra are usually recorded as frequency
measurement called wave number (cm-1) which is the inverse of the true wavelength λ in centimeters to give convenient
numbers (400-4000 cm-1) [11-13]. Higher numbers are to the left of the spectrum because it is really wavelength that is
being scanned. The infrared spectra of pyridine chalcone were recorded on a Perkin- Elmer Spectrum RX-IFTIR
Spectrophotometer over the range 4000-400 cm-1 using KBr pellet at CIL, Chandigarh, Punjab. The Infrared spectrum
of pyridine chalcone is represented figure (2) and the stretching frequency for different groups in table no. (3).
3.3 Electronic absorption spectrum
The absorption of ultraviolet (UV) or visible light results in a change in energy of absorbing molecule. The electronic
spectrum consists of bands containing several absorption lines. Each band corresponds to a definite change in the
electronic energy. The ultra violet visible spectrum of pyridine chalcone shows that major absorption bands usually
occur in the range 230 to 490 nm. The electronic absorption spectrum is given in figure no. (3) and corresponding data
in table no. (4).
1
3.4 H NMR spectral study of Pyridine chalcone
Nuclear Magnetic Resonance Spectroscopy is possible due to the absorption of energy at particular frequency by atomic
nuclei, characterized by a property, termed spin and this gives rise to a magnetic moment associated with that nuclei.
The frequency at which proton absorbs energy depends on electronic environment present around that proton. The
chemical shift () of proton depends upon the factors such as electro negativity, electron density which causes particular
nuclei to appear at different chemical shift ().Greater the shielding effect, lower the chemical shift and opposite of this
character is deshielding effect. In the analysis of organic molecule, 1H NMR spectra plays very important role. It is a
most valuable technique in structural investigation [14]. The 1H NMR spectrum of pyridine chalcone is recorded on
Bruker AVANCE II 400 MHz Spectrophotometer in DMSO solvent using TMS as an internal standard at SAIF,
Chandigarh, Punjab are shown in figure (4) and spectral data in table no. (5).

OH KOH, Ethanol OH
+
CH3 H N
N 3 hours

OH O O O
OH
Fig. (1): Reaction of Pyridine chalcone.
RC SAIF PU, Chandigarh

84.6

80
4 21.1
517 .4 4 09.5
75 4 57.7

70

65 625.3

60
1 051 .7 946 .3 8 56.1
55 9 96.0 774 .5
1022 .9 568 .2
170 3.3 115 1.6
%T 50 305 4.6 1 666.1 7 51.0
3 006 .3 2 657 .4
45 284 9.6 109 9.1
2 918 .3 134 2.1
128 6.6
40

35 1 233 .8
1 367 .9
30

25 1 597 .9
143 5.0
20.0
4 000.0 360 0 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400.0
c m- 1
Ippe r SN- 3.sp - 4/13 /20 18 - A5

Fig. (2): Infra red spectrum for Pyridine chalcone.

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International Journal of Application or Innovation in Engineering & Management (IJAIEM)
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Volume 7, Issue 8, August 2018 ISSN 2319 - 4847

Fig. (3):Electronic absorption spectrum.

B
BRUKER
8.5159
8.2147
7.9560
7.8949
7.7868
7.7692
7.7034
7.6951
7.6917
7.6826
7.5804
7.5608
7.5430
7.5239
7.5045
7.4816
7.4695
7.4477
7.4056
7.3898
7.3715
7.3472
7.3279
7.3111
7.2883
7.2743
7.2566
7.2411
7.1211
7.1104
7.0843
5.8705
3.4753
3.4577
3.4403
3.4228
3.3612
3.3436
3.3382
3.1769
2.8865
2.7315
2.7163
2.7066
2.7008
2.6901
2.6848
2.6656
2.6512
2.6465
2.6352
2.6121
2.6057
2.5995
2.5858
2.5607
2.5458
2.5147
2.5112
2.5068
2.5023
1.9184
1.2290
1.0795
1.0620
1.0446
AVANCE II 400 NMR
Spectrometer
SAIF
Panjab University
Chandigarh

Current Data Parameters

NAME Feb21-2018
EXPNO 480
PROCNO 1

F2 - Acquisition Parameters
Date_ 20180222
Time 9.59
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT DMSO
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 161
DW 41.600 usec
DE 6.00 usec
TE 295.4 K
D1 1.00000000 sec
TD0 1

======== CHANNEL f1 ========

NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz

F2 - Processing parameters
SI 32768
SF 400.1300000 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
1.64

0.27

3.52

5.03

8.59

2.15

6.02

1.06
1.95
1.81
3.22

1.01
0.98

16 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm

manishkumarmanu1986@gmail.com

Fig.(4): 1H Nuclear Magnetic Resonance Spectrum of pyridine chalcone

Table no. (1): The properties of pyridine chalcone

Property Color M.P. Yield Chemical Chemical Molecular Phase

0c name formula weight

Observation Yellow 255 90 % Pyridine C14H 11O3N 241 Solid(Yellowish

chalcone brown crystals)

Table no. (2): Elemental analysis data of Pyridine chalcone (C14H11O3N) and chemical structure.
7.49 7.61
CHO analysis Calculated in % 6.48
8.11
OH
H
5.0
7.20
7.27
C H O N
N
6.48 8.63
H
8.17

68.69 4.61 20.94 5.80 OH

5.0
O

(69.70) (4.60) (19.90) (5.81)

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Table no. (3): The stretching frequency of different groups

(-CO-CH=CH- Aromatic
υ(OH) ) α, β- (C-O-C) (C=C) Ring Ar-H
unsaturated Stretching Stretching (C=C) Stretching
Enolic carbonyl Frequency Frequency Stretching Frequency
group Frequency
3055 cm-1 1666 cm-1 1099 cm-1 1597 cm-1 1435 cm-1 3001 cm-1

Table no. (4): Electronic absorption spectrum: absorption and corresponding wave length for Pyridine chalcone.
Absorption spectra Wavelength

absorbance λ(nm)
3.0392 260
3.4037 302
3.5364 329

Table no. (5): 1H Nuclear Magnetic Resonance Spectral data of pyridine chalcone

Chemical Shift Number of Multiplicity Assignment

(s) ppm
Protons (Splitting)

6.48-7.20 3H m Aromatic protons

5.0 2H S -OH group present on aromatic

benzene ring.

8.17 1H d α-H on-unsaturated carbonyl system

8.11 1H d β-H on-unsaturated carbonyl system

7.27-8.63 4H m Protons on pyridine ring..

4. CONCLUSION
The Pyridine chalcone having IUPAC name 1-(2, 6-di-hydroxyphenyl)-3-(1 H-pyrrole-2-yl) prop-2-en-1-one were
synthesized by Claisen-Schmidt condensation method and its structure is confirmed by IR , 1HNMR, UV spectra, CHO
analysis, physical properties, Wilson’s test, FeCl3 test and unsaturation test with KMnO4. This is novel Pyridine
chalcone. The reaction mechanism for the formation of Pyridine chalcone shows condensation of aldehyde group of
pyridine and ketone group of 2, 6-di-hydroxy acetophenone takes place.

5. ACKNOWLEDGEMENT
Authors are thankful to Principal, Sunderrao Solanke Mahavidyalaya, Majalgaon Distt:Beed (India) for providing
laboratory facilities.

REFERENCE
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Encyclopedia of Industrial Chemistry, A22, 399, VCH Publishers,2000.

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International Journal of Application or Innovation in Engineering & Management (IJAIEM)
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AUTHOR
Mr. Shankar Ipper Recieved M.Sc Degree in Chemistry from Yeshwant College Nanded Affilated
to Swami Ramanand Teerth Marathwada University Nanded in 2004. Woking as Assistant Professor
in Sunderrao Solanke Mahavidhyala Majalgaon District Beed. In Maharashtra India.

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