2-Nitrobenzoyl chloride → 2-(Aminomethyl)aniline

Participants

Reaction Steps

N-(2-Aminobenzyl)-2-nitrobenzamide was itself obtained as a solid, m.p. 112-113° C., in 80% yield using a similar procedure to that described for the starting material of Example 24, that is by reacting 2-nitrobenzoyl chloride with 2-aminobenzyl (J.Amer.Chem.Soc., 1949, 71, 2137) except that, after the work-up described therein was complete, the residue was triturated in a mixture of diethyl ether/methylene chloride/methanol (1/1/ few drops v/v). The crystalline solid, formed by reaction of the acid chloride with both of the amino groups of 2-aminobenzylamine, was filtered off and discarded. The residual solution was concentrated and N-(2-aminobenzyl)-2-nitrobenzamide was precipitated by the addition of diethyl ether.

Provenance & Evidence