SCHEDULED MAINTENANCE
The reaction of N-(4-chlorobutyryl)isatin (4) with potassium hydroxide is shown to be solvent dependent. In protic solvents (water or ethanol) it gives rise to 2-(2-oxopyrrolidin-1-yl)phenylglyoxylic acid (5) and in aprotic solvents (benzene or dimethylformamide) to N-(3-carboxypropyl)isatin (8). The conversion (5)→(8) is brought about in aprotic medium.
P. Lakshminarayana, K. K. Balasubramanian and P. Shanmugam, J. Chem. Soc., Perkin Trans. 1, 1973, 998 DOI: 10.1039/P19730000998
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