World Journal of Pharmaceutical Research

Vyas et al. World Journal of Pharmaceutical Research

SJIF Impact Factor 6.805

Volume 5, Issue 5, 928-931. Research Article ISSN 2277– 7105

PREPARATION AND CHARACTERIZATIONS OF (2E)-1-(4-{(E)-

[(3,4,5-TRIMETHOXY PHENYL) METHYLIDENE]AMINO}PHENYL)-
3-PHENYLPROP-2-EN-1-ONE

S. P. Vyas*, K. M. Daraji, P. P. Darji, P. A. Patel, T. K. Goswami and K. V. Goswami

Organic Chemistry Research Lab., Chemistry Division, The H.N.S.B. Ltd. Science College,
Himatnagar -383 001.

ABSTRACT
Article Received on
02 March 2016, In this present study, p-amino acetophenone condensed with
Revised on 23 March 2016, benzaldehyde in ethanolic solution of sodium hydroxide to yield
Accepted on 12 April 2016
DOI: 10.20959/wjpr20165-6095 corresponding chalcone, which reacts with aromatic aldehydes in
glacial acetic acid to yield corresponding Schiff bases. Final moieties
have been characterized by FT-IR, 1H NMR and Mass Spectra.
*Corresponding Author
S. P. Vyas
KEYWORDS: Preparation, Characterization, Chalcone & Schiff base.
Organic Chemistry
Research Lab., Chemistry
INTRODUCTION
Division, The H.N.S.B.
Ltd. Science College, The synthesis of chalcone linked with imine group in same compound
Himatnagar -383 001. became of great importance in organic chemistry to synthesis of
various compounds. α,β-Unsaturated ketones are biogenetic precursors
of flavonoids in higher plants. Also known chemically as halcones, they consist of open-
chain flavonoids in which the two aromatic rings are joined by a three carbon chain.[1,2] They
display a wide range of pharmacological properties, including cytotoxity toward cancer cell
lines[3,4], anti mitotic , anti mutagenic[5] The chemistry of chalcones has generated intensive
scientific interest due to their biological and industrial application. Chalcones are natural
biocides and are well known intermediates in the synthesis of heterocyclic compounds
exhibiting various biological activities[6] Chalcones and their derivatives possess some
interesting biological properties such as antibacterial, antifungal, insecticidal, anesthetic, anti
inflammatory, analgesic. Etc.[7,8] In this research work, we used chalchon and prepare
Schiff-base which have wide range of pharmacological activities like antimicrobial,
antiparasitic, anti-inflammatory, anticancer[9-13] etc.

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Vyas et al. World Journal of Pharmaceutical Research

MATERIALS AND METHODS

Melting point were recorded in open capillaries and on Veergo melting point apparatus. The
1
H NMR Spectra were recorded on a Bruker 300 MHz using TMS as an internal standard.
The IR spectra were recorded on a Perkin Elmer Spectrum 100 FTIR Spectrophotometer and
the Mass Spectra on a Waters Micromass Q-fit instrument. The chemical used are of A.R.
grade.

Preparation of (2E)-1-(4-aminophenyl)-3-phenylprop-2-en-1-one
Equimolar quantities of substituted 4-amino acetophenone (0.675gm., 0.005 mol) and
benzaldehyde (0.530gm., 0.005 mol) were dissolved in ethanol (15 ml), under stirring and
aqueous NaOH (1.1gm. in 10 mL) was added drop wise. The reaction mixture was stirred at
room temperature and kept for 4-6 hours. The reaction mixture was diluted with water and
acidified with 10% HCl. The separated solid was filtered and crystallized using acetic acid to
give compounds.

O
H2N + NaOH

CH3 -H2O
O
1-(4-aminophenyl)ethan-1-one benzaldehyde H2N
(2E)-1-(4-aminophenyl)-3-phenylprop-
2-en-1-one

Preparation of (2E)-1-(4-{(E)-[(3,4,5-trimethoxyphenyl)methylidene]amino}phenyl)-3-
phenylprop-2-en-1-one
A mixture of (2E)-1-(4-aminophenyl)-3-phenylprop-2-en-1-one(1.115gm.,0.005 mol) and
3,4,5-trimethoxybenzaldehyde(0.980gm., 0.005 mol) was taken in absolute ethanol(20 ml.)
and 1-2 drops of glacial acetic acid were added. Then the mixture was refluxed for 6-8 hours
on water bath. The progress of the reaction was monitored by TLC. The excess solvent was
distilled off and then Remaining residue was poured in crushed ice. The separated solid was
filtered, washed and recrystalized from ethanol.

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Vyas et al. World Journal of Pharmaceutical Research

CH3 Acid catalyst

CH3 O O
-H2O
O
+ O
N
H3C O O
O H2N
H3C
3,4,5-trimethoxybenzaldehyde (2E)-1-(4-aminophenyl)-3-phenyl
prop-2-en-1-one O
CH3 O
CH3

Table: Physicochemical characterization data for chalchon & Schiff base

Comp. Molecular Molecular M.P Yield % of % of % of
Name formula weight °C % C H N
Kpp-1 C23H19N 309.40 200 79.35 89.28 6.19 4.53
Kpp-2 C25H23NO4 401.45 60 37.80 74.79 5.77 3.49

Spectra study of (2E)-1-(4-{(E)-[(3,4,5-trimethoxyphenyl)methylidene]amino}phenyl)-3-

phenylprop-2-en-1-one
IR(KBr. cm-1):1622 cm-1(C=N),1235 cm-1(N=CH str), 1036 cm-1, 1010(CH=N),3420 cm-1
(N-H),1438 cm-1 (C=N, Ar), 1H NMR(ppm) (CDCl3):5.56(s,1H,Ar-H),6.66-6.68(m,4H,Ar-
H),2.59(s,3H,CH3), MS:402.45[M+1].

RESULTS AND DISCUSSION

4-aminoacetophenone react benzaldehyde room temp. and base catalyst reaction and we got
(2E)-1-(4-aminophenyl)-3-phenylprop-2-en-1-one, further its react with 3,4,5-trimethoxy
benzaldehyde in presence 1 ml. of glacial acetic acid gave Schiff base. Title moieties
synthesized were adequately characterized by their elemental analyses and spectral IR,
1
H-NMR and Mass Spectra.

ACKNOWLEDGEMENTS
We are thankful to The H. N. S. B. Ltd. Science college, himmatnager for providing excellent
facilities and we are also grateful to our guide Dr. S. P. Vyas Sir and M.Sc. (Organic
Chemistry) PG-Incharge Dr. Z. M. Gadhawala sir.

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