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Chapter – 4 Studies on different types of reactions…..
4.2 INTRODUCTION TO OXINDOLE
Oxindole (1, 3-dihydro-2H-indol-2-one; C8H7NO) is an aromatic
heterocyclic organic compound. It has a bicyclic structure, consisting of a sixmembered
benzene ring fused to a five-membered nitrogen-containing ring.
The compound's structure is based on the indoline structure but where a
carbonyl is situated at the 2-position of the five-membered ring.
4.2.1 PHYSICAL PROPERTIES OF OXINDOLE
Oxindole crystallizes from water in colourless needles melting at 126-
127°C. The substance boils at 195°C at 17 mm a and at 227°C at 73 mm. 21 It
is soluble in hot water, alchohol, benzene, ether and acetic acid. It is more
soluble in alkaline solutions than in water. The heat of combustion at constant
volume has been found to be about 950.5 kg.-cal./mole. b
The chemistry of indoles especially that of oxindole derivatives dates
back to 134 years old when first Baeyer 20 published the results of his
researches on the reaction of isatin. In addition to isatide, which had been
obtained previously by Laurent 21-23 and by Erdmann, 24 Baeyer obtained
dioxindole (C8H7NO2) by the further reduction of which oxindole was
prepared. Baeyer established the constitution of oxindole as the lactam of 2aminophenylaceticacid
through its synthesis by the reduction of 2-
a A. Waul and P. Bagard; Compt. rend., 1910, 149, 132.
b M. Berthelomt and G. Andre; Compt. rend., 1899, 128, 970.
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Department of Chemistry, Saurashtra University, Rajkot – 360 005 190
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Fig. 4.1
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