p-Toluenesulfonic acid → Butanoic acid, 3-[[5-(acetylamino)-2-methoxyphenyl]amino]-, ethyl ester

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Reaction Steps

A mixture of 105.0 g. (0.5 mole) of 2-nitro-4-acetamidoanisole, 67.0 g. (0.5 mole) of ethyl acetoacetate, 550 ml. of isopropyl alcohol, 10.0 g. of 5% Pt/C, and 3.0 g. of p-toluenesulfonic acid is treated in an autoclave at 165° C. and 1,000 psi of hydrogen until the uptake of hydrogen ceases. The solvent and catalysts are removed. Upon standing, 143.8 g. (98%) of ethyl 3-(2'-methoxy-5-acetamidoanilino)butyrate is obtained. NMR analysis of the product supports the proposed structure.

Provenance & Evidence