An Organic Lab Experiment On The Michael Addition

Preparation of
1-Phenyl-3-phenylaminopyrrolidine-2,5-dione
An Organic Laboratory Experiment on the Michael Addition
Ram N. Ram1 and Kiran Varsha
Indian Institute of Technology, Delhl Hauz Khas, New Delhl-110016, India

The Michael Addition is one of the important synthetic methods for the preparation of 1,3- and 1,5-difunctionalized compounds ( I ) . Virtually all undergraduate organic chemistry textbooks use a consideration of the Michael addition, hut few suitable laboratory experiments have been puhlished on this subject to supplement the lectures. Most of the reported procedures (2) suffer from one or more of the following disadvantages-long reaction time ranging from several hours to days, lengthy product isolation and …show more content…

3 . 3 8 r l H , d d . H n , J . ~ n =
1RHz.Jnx =
R H rJ.4.46 I lH, d d, Hx, J ,x = 6 H z I , ~ ,=, R Hz),6.61-7.4: rlOH,
~
m , aromatic) ppm

986

J ournal

of

C hemical Education

Method B
A mixture of maleie anhydride (3 g, 30 mmol), aniline (6 g, 64 mmol). and elacial acetic acid (10 mL) is refluxed for 90 min. The solid obtain& after cooling is filtered,washed with a little ethanol, and dried to get compound 2 (3.8 g, 41%).
A cknowledgment
Financial s u p p o r t t o K. V. b y the CSIR, N ew Delhi, is g ratefully acknowledged.
Literature Cited
1. Warren. S. O r p n i e gvnfhesk: The Disronnecrion Approach; Wiloy:

New York, 1982: pp 48,170.
2. Furniss. 8 . S.: Hannaford, A . J.; Rogers, V : Smith, P. W. G .; Tafehell. A. R. Vogrl's
Textbook o f P r a r f i ~ o O ~ g n n i r hemistry, 4 th ed.; Longman: London, 1978; p p494l
C
497,525-527,555,656;Cason.
J.;Rspporf, H L o b o r a l o ~ ext i n01ganie C hem~stry,
.
T
2nd ed.: Prentice-Hall: Englewood Cliffs, N J, 1962: p 390: G a r e i a - k o , A,: GarciaRsso. J.:Sinisfprra.J. V.: Mestre.. R . J . C h e m E d u c . 1986.63.443.
1 I n l a - , , e wnl) thr. .rch a r s h r e \ t m s . < c c ollertlon . I r ~ ~ ursanh l elrrnl r ) nl i.r*r r wp oc i n* n n t n c w o i u lan~sl; Y e!dcd I n r ru , r onq~.e. I. 11, w n a r chm. lhnr T ur\ccs?c?src . A.lt,A I ? , < " jb. , a ? 2 K x r . e r . n . . n ~ ~rl c ~ r . m . f 1 , 3 .z.
, . , r ) 5 1 h d . .\l.vn*nd n a. 11 Rn.tm. 1s.-