Formanilide, hydrolysis

Robinson and Jencks118,119,165,228 have made detailed kinetic studies of the hydrolysis of several imidazolinium cation derivatives. With the aid of stopped-flow studies, all rate and equilibrium constants shown have been evaluated118,119,228 at 25° for the ring opening of the 1,3-diphenylimid-azolinium cation (63) in aqueous base to N-(2-anilinoethyl) formanilide (64). Kinetic studies165 of the hydrolysis of the N5,10-methenyltetrahydrofolate... 

In early work Pictet and Crepieux489 alkylated formanilide in the presence of alcoholic potassium hydroxide and obtained monoalkylanilines (methyl to pentyl) by hydrolysis (short warming with alcoholic potassium hydroxide or concentrated hydrochloric acid). 

When N-substituted formanilides 1780 are treated briefly and sequentially with oxalyl chloride, Hunig s base, and bromine, isatins 1784 are rapidly formed, many in good yields. The reaction involves deprotonation of the Vilsmeier reagent, dimerization of the carbene thus formed, and electrophilic cyclization of the dimer by the action of bromonium ion followed by aqueous hydrolysis [1309, 1310]. The reaction sequence has been developed into a simple and efficient one-pot isatin synthesis from formanilides. 

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