5-bromo-3-hydroxy-3-[2-(4-methoxyphenyl)-2-oxoethyl]indolin-2-one synthesis

Yield:258264-67-4 86%

Reaction Conditions:

with 1,4-diaza-bicyclo[2.2.2]octane in water at 80; for 3 h;Green chemistry;

Steps:

General procedure: A solution of 0.5 g (3.4 mmol) of isatin (1), 0.408 g (3.4 mmol) of acetophenone (2), and 0.080 g (0.72 mmol) of DABCO in water (15 mL) was heated to 80 °C for 1-3 hours. After the completion of reaction, which was indicated by TLC, the solid that separated out was collected and washed with water. In some cases, the reaction mixture was extracted with ethyl acetate as the solid was not getting filtered off and the combined organic layer was evaporated to give the solid reaction mixture. Although the TLC indicated the completion of both starting materials, the reaction mixture was purified by column chromatography on silica gel by using 40% of EA/hexane mixture to provide a light yellow product in good to excellent yields.

References:

Tiwari, Keshri Nath;Bora, Darshana;Chauhan, Garima;Yadav, Deepika;Sharma, Kavita;Thakur, Ashima;Singh, Lachhman;Tripathi, Vishwadeep [Synthetic Communications,2016,vol. 46,# 7,p. 620 - 625]