Step 2

Procedure

Pyrogallol ( …g , 2mmol) was stirred under reflux with Piperidine base in ethanol solvent for 45
minutes. Then 2-(2-oxindoline-3-ylidene)malononitrile(74) ( ….g , 1mmol) was added and
stirred for 6 hours under reflux. The mixture then filtered and silica was added which kept for
whole night. The pure product extracted by column chromatography using ethyl acetate-
petroleum ether (3:2) solvent system. The pure yellow coloured product analysed using IR
spectroscopy, melting point and single spot TLC with 60% yield.

Physical characteristics:-

Colour: yellow colour

Nature: sticky solid product

2-11,1 Infra red Analysis Of the Compound ( 76 )

compound (76) ( …g , 1mmol) in 1ml distilled ethanol was stirred at 90°C for 45 minutes, then
1N NaOH (1ml ) solution was added and stirred the mixture at 110°C for 3 hours. The
mixture neutralized with 1N HCl solution and dark yellow coloured hydrolysed product (77)
obtained, purified using column chromatography. The pure product (77) was analysed using IR
spectroscopy, melting point and single spot TLC.

Physical appearance of product (77) = dark yellow coloured

2-12.4 IR Analysis of product of Product (77)

Following peaks appeared in IR spectrum

Functional group Stretching frequencies ( cm- )

 -NH2 3500

C=C 1640

AROMATIC C = C 1675

Carboxylic acid -COOH 3500 – 3300 broad band

Alcohol -OH 3200 – 3400 broad band

5-nitroisatin synthesis

PROCEDURE

A solution of potassium nitrate (KNO3) (344mg, 3.4 mmol) in concentrated sulfuric acid (3.8
mL) was added dropwise to an isatin (0.5g, 3.4 mmol) solution in concentrated sulfuric acid
(H2SO4). The temperature was held at 0 to 4 °C. The mixture of the reaction was added to 25
mL of ice-cooled water. The precipitates were gathered and given another water wash. Crude 5-
nitroisatin was purified using recrystallization and pure product ( 78) was obtained.