R.C.PATEL A.C.

S COLLEGE, SHIRPUR
DHULE

Project Report Entitled

“ Molecular Iodine Catalysed Simple and Efficient
Synthesis of Indazole.”
Submitted by
Mr. Jagtap Rushikesh R.
Under The Guidance of
Mr. V.S. Patil (Asst. Prof.)

Principal
Dr. D.R.Patil
(M.Sc.,PhD.)

R.C.PATEL ACS COLLEGE SHIRPUR

 R.C.PATEL ACS . COLLEGE SHIRPUR
DEPARTMENT OF CHEMISTRY
CERTIFICATE
This is to certifie that the work incorporated in the project
report entitled “molecular iodine catalysed simpal and
Efficient synthesis of indazole..Submitted by MR. Jagtap
Rushikesh R. for the award of the degree of master of
science in chemistry By department of chemistry was
carried out by the candidate under the supervision of prof.
Mr. V.S.Patil (Assistant Prof.)division of organic chemistry
RC PATEL ACS.College Shirpur

HEAD Project Guide

Department of chemistry Mr. Prof.V.S. Patil
Dr.J.P. Mahashabde
Date / /2020

Place : Shirpur
 R.C.PATEL ACS COLLEGE SHIRPUR
DEPARTMENT OF CHEMISTRY
GUIDE CERTIFICATION

This is to certify that the project report on ‘’MOLECULAR

IODINE CATALYSED SIMPLE AND EFFICIENT SYNTHESIS OF
INDAZOLE ’’ Has been submitted by Mr.Jagtap Rushikesh
R.In partial fulfillment of degree of master of science in
organic chemistry under my guidance and supervision in
department of chemistry under the aegis on K.B.C.North
Maharastra university Jalgaon.

Project Guide
Prof.Mr.V.S.Patil
Department of Chemistry

R.C.PATEL COLLEGE SHIRPUR

Date: / /2020

Place:
 DECLARATION
We have here sincerely declared that the
project entitle “Molecular Iodine Catalysed
Simple and Effficiant Synthesis Of Indazole ”
Was done by under the External guidance of
Prof.Mr.V.S.Patil division of organic
chemistry R.C.Patel ACS.College Shirpur

Submitted By
Mr. Patil Kunal S.
Mr. Patil Prashant P.
Mr. Patil Dhiraj R.
Mr. Kumbhar Rakesh D.
Mr. Jagtap Rushikesh R.
 ACKNOWLEDGMENT
It gives a great pleasure express our sincere
gratitude towards Prof.Mr.V.S.PATIL Guide for
inspiring stimulating discussion and constant
encouragement throughout the project work.
We have the honor to express our deep sense of
and heartiest thanks to Dr. D.R.PATIL Principle of
R.C.PATEL ACS COLLEGE Shirpur for making all
possible facilities available to us.
Our acknowledgment remain incomplete thank
teaching and non-teaching staff of chemistry
department. We are also thankful to our
colleagues for their co-operation and friendly help
throughout the project.
We cannot express our deep gratitude to all by
merely saying “Thank you” but we humbly prefer
to remain under obligation to all of them.
 INDEX

 Acknowledgement
 Introduction
 Experimental details
 Spectra (IR)
 Result and Conclusion
 Reference
 Introduction
Indazole , also called isoindazole,is a heterocyclic aromatic
organic compound
indazole was first defined by scientist Emil fisher as a
"pyrazole ring fused with benzene ring

N
N
H
Indazole derivatives are involved in a variety of biological
activity such as analgesic anti-inflammatory ,antipyretic ,
antiemetic,antidesprssant,anticancer and anti-HIV activitie.
The indazole derivatives are pharmacologically importnt
compounds as their ring system forms number of
molecule,such as granisetron which are used as an anti-
emetic in cancer chemotheropy ad benzyamine as,an
antiinflammatory agent.
In recent years ,the use of molecular iodiene in organic
synthesis has received considerable attention because of
numerous advantage associated with these cosiderable
element,iodine has been explored as a powerful catalyst
forvarious organic transformations.The acidity of iodine
makes it capable of binding with the aldehyde carbonyl
oxygen,incresing the reactivity of the parent carbonyl
compound.
Several other catalyst reported for synthesis of indazol but
they have certain limitations such as long reaction
time,difficult in work up
K3PO4,CuO,Pd(dba),SSA,montmorillonite K-10.
Recently,molecular iodine has attracted attention as a
simple,in expensive and non-toxic reagent in organic
synthesis.
We reporthere the synthesis of indazol from ortho
hydroxyaldehydes by using hydrazin hydrate in solvents like
Menthol,Ethanol,Acetonitrile,Toluene,THF,DMFand
DMSO.But DMSO gives good yield in camparison to the other
solvents by using catalysic amount of molecular iodine In
comparison to.
The Iodine is used as catalyst in reaction,it’s incries in rate of
reaction. The use of molecular ioine in organic synthesis has
received considerable attention as an inexpensive ,non-
toxic,readily available mild Lewis acid catalyst for organic
synthesis benzothiophens,bis indoles,quinoxaline
derivatives,deprotection
acetals,estrificaton,Transestrification and Michel additon.
Recently we have reported the use of iodine for the synthesis
of an indzol.
 EXPERIMENTAL SECTION
Procedure:-1
Take 10 ml of DMSO solvent in beakar and 2-
clorobenzaldehyde 7.11mmole (1.00gm) hydrazine
7.11mmole(0.35) and iodine 0.711 mmole (0.18) place
the mixture for stirring at room tempreture for one
hour pour this mixture in 50 ml water and filterthe
precipitate, dry and recrystalise from ethanol record
the yield and physical constat.

Reaction:-

.
Mechanism(A):-

EXPERIMENTAL SECTION
Procedure: - 2
Take 10ml of DMSO solvent in beaker and
2-chlorobenzaldehyde 7.11 mmole (1.00gm) in 2,4
Dinitro phenyl Hydrazine 7.11mmole (1.40gm) and
iodine 0.071 mmoles (0.09gm) place the mixture for
stirring at Room temperature at 1hr, then ppt is often
and pour the in 50ml water and filter the precipitate dry
and Recrystalise the product. Record the yield and
physical constant.
Reaction:-
Mechanism(B):-
.

. EXPERIMENTAL SECTION
Procedure:-3
Take 10 ml of DMSO solvent in beakar and 2-
Hydroxybenzaldehyde 7.11mmole (1.00gm) hydrazine
7.11mmole(0.35) and iodine 0.711 mmole (0.18) place
the mixture for stirring at room tempreture for one
hour pour this mixture in 50 ml water and filter the
precipitate, dry and recrystalise from ethanol record
the yield and physical constat.

Reaction:-

. Mechanism(c):-
 EXPERIMENTAL SECTION
Procedure: - 4
 Take 10ml of DMSO solvent in beaker and 2-
Hydroxybenzaldehyde 7.11 mmole (1.00gm) in 2,4
Dinitro phenyl Hydrazine 7.11mmole (1.40gm) and
iodine 0.071 mmoles (0.09gm) place the mixture for
stirring at Room temperature at 1hr, then ppt is often
and pour the in 50ml water and filter the precipitate
dry and Recrystalise the product. Record the yield and
physical constant.

Reaction:-
Mechanism(D):-
 EXPERIMENTAL SECTION
Procedure:-5
Take 10 ml of DMSO solvent in beakar and 2-
Bromobenzaldehyde 7.11mmole (1.00gm) hydrazine
7.11mmole(0.35) and iodine 0.711 mmole (0.18) place
the mixture for stirring at room tempreture for one
hour pour this mixture in 50 ml water and filter the
precipitate, dry and recrystalise from ethanol record
the yield and physical constat.

Reaction:-

.
Mechanism(E):-
 IR SPECTRUM
IR Of Indazole
IR Of 1-(2-4 Dinitrophenyl)1-H-Indazole
Result Table:-
Reactant Reagent Solvent Time %Yield Melting
Point
2-chloro Hydrazine DMSO 1.30 86.66% ◦
152 C
benzaldehyde Hours
2-chloro 2,4 DMSO 1.15 89.10% ◦
212 C
benzaldehyde Dinitro Hours
phenyl
hydrazine
2-Hydroxy Hydrazine DMSO 1.30 87.20% ◦
153 C
benzaldehyde Hours
2-Hydroxy 2,4 DMSO 1.15 86.20% ◦
214 C
benzaldehyde Dinitro Hours
phenyl
hydrazine
2-Bromo Hydrazine DMSO 1.30 87.71% ◦
155 C
Benzaldehyde Hours
 CONCLUSION
In summary a highly efficient
methodology for the synthesis of substituted
indazole by condensation of orthochloro,
orthobromo, orthohydroxy carbonyl
compound and hydrazine, 2,4dinitrophenyl
hydrazine in presence of catalytic quantity of
iodine is reported. This procedure is simple,
efficient gives high yield of product at room
temperature.
 REFERENCES

1. J.A.Ma.A.P Dantanarayana,P.W.Zinke,M.A.McLaugblia and

N.A.Sharif,J.Med.Chem;2006
2. K.Banno,T.Kawahata,T.Ikeda,k.Nakagawa and T.Dohi,Japanese
Patent,1973
3. Schumann,p;collot,v;Homment,Y,Gsell,W;Dauphin,F;Sopkova,j;Mackenzi
e,E,t;Duval,D;Boulouard,M;Rauli,S.2011
4. Park,J,S;Yu,K,A;Kang,t,h;Kim,S;Suh,Y.G2007
5. Bermudez J, Fake CS, Joiner GF, Joiner KA, King FD, Miner WD,Sanger GJ
(1990) J Med Chem 33:1924–1929
6. Bistochi GA, De Meo G, Pedini M, Ricci A, Brouilhet H, Bucherie S,
Rabaud M, Acquignon P (1981) , FarmacoEd Sci 36:315–333
7. Kimball, D. B.; Hayes, A. G.; Haley, M. M. Org. Lett. 2000, 2, 3825-3827.
8. Sharples, D.; Hajos, G.; Riedl, Z.; Csanyi, D.; Molnar, J.; Szabo, D. Arch.
Pharm. 2001, 334, 269-274.
9. Steffan, Robert John et alFrom PCT Int. Appl., 2004031159, 15 Apr 2004