A rapid synthesis of N-aryl phthalimides under microwave irradiation in the absence of solvent

Article abstract of DOI:10.1081/SCC-120002706

A mixture of phthalic anhydride (1) and aromatic amines (2a-h) were irradiated in a microwave oven for 2-10 min to provide N-aryl phthalimides (3a-h) in 91-95% yields.

Full text of DOI:10.1081/SCC-120002706

This article was downloaded by: [Memorial University of Newfoundland]
On: 04 August 2014, At: 04:08
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House,
37-41 Mortimer Street, London W1T 3JH, UK
Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic
Chemistry
Publication details, including instructions for authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
A RAPID SYNTHESIS OF N-ARYL PHTHALIMIDES UNDER
MICROWAVE IRRADIATION IN THE ABSENCE OF SOLVENT
a
a
a
a
Hui-Zhang Li , Jin-Song Zhang , Ya-Ming Zhou & Tong-Shuang Li
a
College of Chemistry and Environmental Science , Hebei University , Baoding, 071002, P.R.
China
Published online: 16 Aug 2006.
To cite this article: Hui-Zhang Li , Jin-Song Zhang , Ya-Ming Zhou & Tong-Shuang Li (2002) A RAPID SYNTHESIS OF N-ARYL
PHTHALIMIDES UNDER MICROWAVE IRRADIATION IN THE ABSENCE OF SOLVENT, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 32:6, 927-930, DOI: 10.1081/SCC-120002706
To link to this article: http://dx.doi.org/10.1081/SCC-120002706
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained
in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the
Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and
should be independently verified with primary sources of information. Taylor and Francis shall not be liable for
any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever
or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of
the Content.
This article may be used for research, teaching, and private study purposes. Any substantial or systematic
reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any
form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://
www.tandfonline.com/page/terms-and-conditions

SYNTHETIC COMMUNICATIONS, 32(6), 927–930 (2002)
A RAPID SYNTHESIS OF
N-ARYL PHTHALIMIDES
UNDER MICROWAVE IRRADIATION
IN THE ABSENCE OF SOLVENT
Hui-Zhang Li,* Jin-Song Zhang,
Ya-Ming Zhou, andTong-Shuang Li
College of Chemistry and Environmental Science,
Hebei University, Baoding 071002, P.R. China
ABSTRACT
A mixture of phthalic anhydride (1) and aromatic amines
(2a–h) were irradiated in a microwave oven for 2–10 min to
provide N-aryl phthalimides (3a–h) in 91–95% yields.
Phthalimide derivatives have attracted considerable attention owing to
their effective biological activity and extensive use.The reported general
1
methods for the synthesis of N-aryl phthalimides need long time reflux.
In recent years, microwave irradiation, as a high energy technique, has
been used in organic synthesis.
2
–7
This paper has discussed the synthesis
of a series of N-aryl phthalimides by reaction of phthalic anhydride with
arylamine under microwave irradiation in the absence of solvent (scheme).
The results show microwave irradiation can enhance the reaction.When
compared to classical heating, the reaction time were improved (Table 1).
*
Corresponding author.E-mail: zjs2000@fm365 c. om
27
9
Copyright & 2002 by Marcel Dekker, Inc.
www.dekker.com

9
28
LI ET AL.
Scheme.
EXPERIMENTAL
Melting points were uncorrected and were measured with micro-
melting point apparatus.IR spectra were recorded on a PE-983G
1
spectrometer (KBr). H NMR spectra were measured on a Bruker AC-80
spectrometer (TMS, DMSO).Mass spectra were determined on a VG-
7070E spectrometer (EI, 70eV).Microwave irradiation was carried out
with commercial microwave oven (2450 MHz).
General procedure. A mixture of phthalic anhydride (1, 15 mmol) and
an aromatic amine (2, 10 mmol) in an open container was introduced into
the microwave oven and irradiated for 2–10 min (output power at 100%) as
indicated in Table 1.The reaction was monitored by TLC till the products
disappeared.Upon completion, EtOH (95%, 10 ml) was added to the reac-
tion mixture which was heated to reflux for 10 min.After cooling, the prod-
uct was filtrated to give a white solid.The crude products were
recrystallizated from EtOH or CH COOH to give a series of N-aryl phtha-
3
limides in 91–95% yields.
The melting points, 3a–h agreed well with those reported (Table 1).
8
–9
1
The IR and H NMR data 3a, 3c, 3e–h were shown as following.
Table 1. The N-Aryl Phthalic Anhydride with Aromatic Amines Under
Microwave Irradiation (650 w)
ꢀ
ꢀ
Reaction
Time (min)
Yield
(%)
M.P. ( C)
(Reported)
M.P. ( C)
(Found)
Compounds
Ar-
8
3
3
3
3
3
3
3
3
a
b
c
d
e
f
C
p-CH
p-ClC
6
H
5
ꢁ
3
4
3
3
2
3
10
2
93
92
91
92
94
95
94
93
206
209–210
205–206
195–197
159–160
205–206
264–266
184–185
221–222
9
3
C
6
H
4
ꢁ
204
194–195
9
6
H
4
ꢁ
9
o-MeOC H ꢁ
155–156
203–204
264–266
184–185
6
4
9
p-BrC
p-O NC
6
H
4
ꢁ
9
2
6
H
4
ꢁ
9
g
h
a-C H ꢁ
1
0
7
9
b-C10
H
7
ꢁ
221–222

N-ARYL PHTHALIMIDES
929
ꢁ
1
3
a: nmax 3030, 1705, 1490, 1385 cm ; dH (80 MHz) 7.9 (4H, br.s,
0 0 0 0 0
þ
,6,7,8-H ), 7.5 (5H, br.s, 2 ,3 ,4 ,5 ,6 -H ) ppm; m/z 223 [M ], 179, 104, 76.
4 5
5
ꢁ
1
3
b: nmax 3020, 2950, 1720, 1515, 1385 cm ; d (80 MHz) 2.4 (3H, s),
H
0 0 0 0
þ
.9 (4H, br.s, 5,6,7,8-H ), 7.3 (4H, br.s, 2 ,3 ,5 ,6 -H ) ppm; m/z 237 [M ],
4 4
7
1
93, 104, 76.
c: nmax 3030, 1720, 1500, 1390 cm ; dH (80 MHz) 7.9 (4H, br.s,
ꢁ
1
3
0
0
0
0
þ
þ
5
2
,6,7,8-H ), 7.5 (4H, br.s, 2 ,3 ,5 ,6 -H ) ppm; m/z 257 [M ], 259 [M þ 2 ],
4
4
15, 213, 178, 104, 76.
ꢁ
0
1
3
d: nmax 3030, 2900, 1720, 1520, 1385 cm ; d (80 MHz) 3.7 (3H, s),
H
0
0
0
þ
7.9 (4H, br.s, 5,6,7,8-H ), 7.3 (4H, br.s, 3 ,4 ,5 ,6 -H ) ppm; m/z 253 [M ],
235, 224, 210, 195, 179, 130, 120, 104, 76.
4
4
ꢁ
1
3
e: nmax 3030, 1720, 1500, 1390 cm ; dH (80 MHz) 7.9 (4H, br.s,
0
0
0
0
þ
5,6,7,8-H ), 7.6 (4H, dd. 2 ,3 ,5 ,6 -H ) ppm; m/z 303, 301 [M ], 259, 257,
4
4
1
78, 104, 76.
ꢁ
1
3f: nmax 3020, 1720, 1570, 1350 cm ; dH (80 MHz) 8.0 (4H, d,
0
0
0
0
þ
5,6,7,8-H ), 8.1 (4H, dd, 2 ,3 ,5 ,6 -H ) ppm; m/z 268 [M ], 238, 222, 178,
166, 104, 76.
4
4
ꢁ
1
3g: nmax 3020, 1720, 1520, 1480, 1380 cm ; d (80 MHz) 8.0 (4H, br.s,
H
0
0
0
0
0
0
0
þ
5,6,7,8-H ), 7.6 (7H, m, 2 ,3 ,4 ,5 ,6 ,7 ,8 -H ) ppm; m/z 273 [M ], 256, 229,
4
7
2
28, 202, 104, 76.
ꢁ
1
3h: nmax 3020, 1720, 1520, 1480, 1380 cm ; d (80 MHz) 8.0 (4H, br.s,
H
0
0
0
0
0
0
0
þ
5,6,7,8-H ), 7.6 (7H, m, 2 ,3 ,4 ,5 ,6 ,7 ,8 -H ) ppm; m/z 273 [M ], 229, 140,
4
7
126, 104, 76.
ACKNOWLEDGMENT
The project was supported by Natural Science Foundation of Hebei
Province.
REFERENCES
1
2
.Prapas, AG J.O. . r gC. hem.
. Gedye, R.; Smith, F.; Westaway, K.; Ai, H.; Baldisera, L.; Laberge, L.;
Rousell, J.Tetrahedron Lett. 1986, 27, 279.
1959, 24, 388.
3
4
. Giguere, R.J.; Bray, T.L.; Duncan, S.M.; Majetich, G. Tetrahedron
Lett. 1986, 27, 4945.
. Bose, A.K.; Manhas, M.S.; Ghosh, M.; Raju, V.S.; Bari, S.S.; Newaz,
S.N.; Banik, B.K.; Chaudhary, A.G.; Barakat, K.J. J. Org. Chem. 1991,
56, 6968.
5. Cablewski, T.; Faux, A.F.; Strauss, C.R. J. Org. Chem. 1994, 59, 3408.

9
30
LI ET AL.
6. Raner, K.D.; Struss, C.R.; Trainer, R.W. J. Org. Chem. 1995, 60, 2456.
7. Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.;
Mathe, D.Synthesis 1998, 1213–1234.
8.Mary, L S. herrill; Florence, L S. chaeffer; Elizabeth P S. hoye rJA. . m.
Chem.Soc. 1928, 50, 477–479.
9.Ian Heilbron; Bunbury, HM ..
Dictionary of Organic Compounds
(Chinese).Scientific Press: China, 1996; 292–295.
Received in the Netherlands March 23, 2001