Abstract
Methyl 2[2-(3- methyl)indolyl]acetate ( 1a), on treatment with sodium hydride and methyl formate, gives methyl (Z) - 2[2 - (3 - methyl)indolyl] - 3 - hydroxyacrylate ( 2a), which is in tautomeric solvent-dependent equilibrium with methyl 2[2 - (3 - methyl)indolinylidene] - 3 - oxopropanoate ( 6). On reaction with phosphoryl chloride in dimethyl formamide, ( 1a) yields methyl (Z) - 2[2 - (3 - methyl)indolyl] - 3 - N,N - dimethylaminoacrylate ( 9) as expected, together with a more complex product derived from ( 9).
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