4-Nitroaniline → 4-Nitroformanilide

Participants

Reaction Steps

To a mixture of 12 ml. of formic acid and 20 ml. of acetic anhydride (which has been stirred at room temperature for 45 minutes) is added 5 g. (0.036 m.) of p-nitroaniline. After stirring for five hours at room temperature, the reaction mixture is filtered to give p-nitroformanilide, m.p. 195°-199° C. The latter, 3 g. (0.018 m.), is hydrogenated at room temperature in a mixture of 150 ml. of ethanol and 0.3 g. of 10% palladium-on-carbon in a Parr apparatus until the calculated amount of hydrogen is absorbed. The catalyst is filtered off and the solvent is removed in vacuo to leave p-aminoformanilide.

Provenance & Evidence