Methane → 4-(4-Phenoxybutoxy)benzene-1,2-diamine

Participants

Reaction Steps

The procedure of the first paragraph of Example 26 is repeated substituting 4-phenxoybutyl bromide for the 3-phenoxypropyl bromide to afford 2-nitro-4-(4-phenoxybutoxy)acetanilide. After treatment at 20°-25° with methanolic-5N aqueous sodium hydroxide, 1.2 g. of the resultant 2-nitro-4-(4-phenoxybutoxy)aniline in a mixture of 20 ml. of methanol and 0.3 g. of 5% palladized charcoal is hydrogenated under ambient conditions. When the theoretical amount of hydrogen has been taken up, the mixture is filtered and the filtrate stripped to afford 1,2-diamino-4-(4-phenoxybutoxy)benzene as a gum.

Provenance & Evidence