Anthranilic Acid → 4,4-Diaminodiphenylmethane

Participants

Reaction Steps

An 2-anilinecarboxylic acid derivative (e.g. sodium 2-anilinecarboxylate) or an 3-anilinecarboxylic acid derivative (e.g. sodium 3-anilinecarboxylate) and aniline are treated with formalin under acidic conditions to give the corresponding 4,4′-diaminodiphenylmethane derivative. This is diazotized using sodium nitrite under acidic conditions in the presence of hydrochloric acid, followed by reaction with sodium azide, to give the desired product.

Provenance & Evidence