1. International Indexed & Refereed Research Journal, January, 2013 ISSN 0975-3486, RNI- RAJBIL- 2009-30097, VOL- IV * ISSUE- 40
Research Paper—Chemistry
Green and Efficient Approach For Synthesis of
2-aminobenzophenone from Isatoicanhyderide Using
Diacetoxy Iodo Benzene
*Mr. Pande G.B.** Dr. Shirodkar S.G.***Mrs. Joshi P.P.
January,2013 **** Mrs. Kendre K.L.
* Dept. of Chemistry, Netaji Subhashchandra Bose College , Nanded
A B S T R A C T
As an alternative reagent to AlCl3, K-10 clay is high molecular weight, stable, non-hazardous. K-10 clay is acidic and has
been successfully used for Friedel Crafts reaction for the conversion of substituted isatoic anhydride to 2-aminobenzophenone
under microwave condition. Herein we report a new and efficient route for the one-pot synthesis of 2-aminobenzophenone
from substituted isatoic anhydride under microwave. Substituted isatoic anhydride were prepared from isatin.
Keywords : 1,4-benzodiazepines, K-10 clay, isatoic anhydride, 2-aminobenzophenone
Introduction: solution was of 30 percent strength aqueous solution.
2-aminobenzophenone derivatives are The reaction was carried out at room temperature, or
important compounds in organic chemistry because of slightly above this (25-650C). The addition of sulfuric
their application in heterocyclic synthesis and acid accelerated the reaction. The reaction mixture was
medicines.12-Amino-benzophenones have been used stirred for 1-2 hours. The desired isatoic anhydrides
as starting material for the synthesis of a wide variety were obtained in a crystalline form during the reaction
of heterocyclic systems, such as fluorenones, acridines, and were isolated by filtering or centrifuging.
acridones, cinnolines, quinazolines, imidazoles,1-2 and O O
3-arylindoles.3-54-arylquinazolones,6-7 4- R3 O R3
arylquinolines,8-10 4-aryl-quinoline-2-ones,11 AcOH, H2O2
polyphenylquinolines,12-16 have been prepared from NH H 2SO4
R2 R2 N O
H
2-aminobenzo-phenones. The pharmacological activity
R1 R1
of 1,4-benzodiazepines17-22 is the most important focus 2
(3a-3e)
3
in the study of the preparation of 2-aminobenzophenone Representative Procedure For The Synthesis Of Sub-
derivatives. See Table 1 stituted 2-aminobenzophenones:
Expetimental: A well stirred mixture of K-10 clay and dry
All the chemicals used were of S.D. Fine chemi- benzene (0.1 m mol) in CH2Cl2 was added isatoic anhy-
cals. All the solvent used were distilled previously. dride chloride (0.1 m mol) at room temperature. The
Clay was purchased from Aldrich chemicals.Melting mixture was then heated in microwave for a range of 5
points were measured in open glass capillaries on a to 6 min. The progress of reaction was followed by TLC.
Perfit Electro-thermal melting-point apparatus and are Resultant mixture was treated with 1 : 1 HCl and ex-
uncorrected. 1H NMR spectra were recorded at room tracted with chloroform. The organic layer was dried
temperature on a 300 MHz. Varian Inova Spectrometer over anhydrous Na2SO4 and concentrated in a rotary
in CDCl3 using TMS as internal standard. ALGdomestic evaporator.
microwave oven was used at 400W power level for all R
the experiments. A LG domestic microwave oven was N H
H
used at 400W power level for all the experiments. The
N O K-10 Clay / Benzene O
reactions were monitored by TLC using pre-coated X1
plates (Merck). Column chromatography was performed O
X1
using Acme silica gel (100-200 mesh). The products X2
O
were also characterized by comparison of their melting
point with literature values. Spectral Analysis :
Representative Procedure For The Synthesis Of Isatoic The structures of the products were confirmed from
Anhydrides: NMR, IR and LCMS. The representative spectral analy-
Isatin was dissolved or suspended in acetic sis for few of the products is given below. The ob-
acid/formic acid and an aqueous hydrogen peroxide served values are in accordance with the literature
solution was added dropwise. The hydrogen peroxide values.
RESEARCH ANALYSIS AND EVALUATION 59

2. International Indexed & Refereed Research Journal, January, 2013 ISSN 0975-3486, RNI- RAJBIL- 2009-30097, VOL- IV * ISSUE- 40
Result And Discussion :
Table No. 1 Analytical Data Of Substituted 2-amino Benzophenones
Sr. No. Product M.P. (0C) Time Yield
H
N H
C.M. M.W. C.M. M.W.
1 121 O
6 hrs 5 min 70% 82%
H
N H
2 Cl
O
114 6 hrs 4.5 min 72% 84%
H
N H
3 O 2N
O
120 7 hrs 5.5 min 64% 72%
H
N H
4 H 3C
O 122 6.5 hr 5 min 78% 84%
CH3 H
5 N H
O
111 6 hrs 5 min 78% 82%
Cl H
6 N H 110 6.5 hrs 5.5 min 72% 80%
O
7 H
N H 108 6 hrs 5 min 75% 80%
O
CH3
H
8 N H
120 6 hrs 5 min 70% 78%
O
Cl
CH 3
9 H
N H 112 6.5 hrs 5.5 min 65% 76%
O
O2 N
CH 3
10 H
N H
O
118 5.5 hrs 5 min 76% 82%
H 3C
CH3
C H3 H
N H
11 O 115 5 hrs 4.5 min 78% 86%
CH3
Cl H
N H
O
12 110 5.5 hrs 5 min 70% 78%
CH 3
H
N H
O
Br
13 105 5 hrs 5 min 70% 82%
2-Amino-5-bromo-benzophenone
Nature Yellow crystals
Mp 106 0 C
1
H-NMR (500 MHz, CDCl3) 5.90 (s,2H ), 6.52 (d,J = 9.2 Hz, 1H ), 7.30 (dd, J = 9.2, 2 Hz,1H), 7.45 (m, 2H),
7.50 (m,2H ), 7.61 (d, J = 8.7 Hz, 2H )
13
C-NMR (125 MHz,CD Cl3) 112.8, 117.0, 126.6, 128.2, 130.1, 132.2, 134.2, 136.3, 137.8, 147.3, 190.1.
IR (KBr) 3411, 3314, 1613, 1585, 1532, 1400, 1314,1142.
LCMS (M+1) = 277
60 RESEARCH ANALYSIS AND EVALUATION

3. International Indexed & Refereed Research Journal, January, 2013 ISSN 0975-3486, RNI- RAJBIL- 2009-30097, VOL- IV * ISSUE- 40
2-Amino- 5,6-dichloro-benzophenone
Nature Yellow crystals
Mp 108 0C,
1
H-NMR (500 MHz, CDCl3) (500 MHz, CDCl3): 4.5 (s,2H ), 6. 70 (d,J =8.7 Hz,1H ),7.35 (d,J = 8.7 Hz,1H ),
7. 5 (m,2H ), 7.6 (t, J = 7.37 Hz,1H ) (d, J= 8.7 Hz,2H )
13
C-NMR (125 MHz,CD Cl3) 117, 122, 125, 129, 130, 130.3, 132,134.5,137,145
IR (KBr) 3462, 3365, 1665, 1619, 1460, 1403, 1314
LCMS (M+1) = 267
2-Amino-3,5-dichloro-benzophenone
Nature Yellow crystals
Mp 94 0 C
1
H-NMR (500 MHz, CDCl3) 6.58 (s, 2H), 7.42 (s, 1H), 7.48 (s, 1H), 7.53 (m, 2H),
7. 62 (m, 1H), 7.67 (d, J = 7.3 Hz, 2H)
13
C-NMR (125 MHz,CD Cl3) 119.57, 119.72, 121. 5,128.8, 129.6, 132.3, 132.56, 133.8, 139.3, 146, 198
IR (KBr) 3462, 3344, 1608, 1573, 1439, 1314, 1153
Mass (M+1) = 267
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