4-Amino-4'-nitrobiphenyl → 4-Amino-4'-(p-nitrophenyl)azobenzene

Participants

Reaction Steps

The preparation of a compound of formula XII in which m is the integer 2 and X is alkoxy and Y is p-nitrophenyl can be carried out, for example, by reacting 4-nitro-4'-aminobiphenyl with 4-nitro-nitrosobenzene, partially reducing the resulting compound with sodium hydrogen sulfide in ethanol according to Houben-Weyl XI/1, 418, to give 4-amino-4'-(p-nitrophenyl)azobenzene, diazotizing this with sodium nitrite and hydrochloric acid, coupling the diazonium salt with phenol and etherifying the resulting compound with a 1-bromoalkane in ethanol in the presence of potassium carbonate and sodium iodide.

Provenance & Evidence