1-Chloro-4-nitrobenzene → 4-Nitrodiphenylamine

Participants

Reaction Conditions

Reaction Steps

Into a suitable reactor is charged 78.5 parts by weight (0.5 mole) of p-nitrochlorobenzene, 93.8 parts by weight (0.65 mole) of sodium formanilide, 96 parts by weight (0.8 mole) of formanilide. The mixture is gradually heated and stirred; and, at about 134° C., evolution of carbon monoxide begins. Heating is continued until the temperature reaches 180°, at which temperature the reaction mixture becomes self-heating. Stirring is continued at 180°. After about two and one-half hours, 18 parts by weight of carbon monoxide are evolved; and reaction is stopped, xylene added, and the xylene solution washed with 250 parts by weight of water, separated from the water and cooled to 10° C. The crystals of 4-nitrodiphenylamine which form are separated by filtration and washed with a little xylene. From the mother liquor a second crop of 4-nitrodiphenylamine is recovered. The yield of 4-nitrodiphenylamine is 86% and conversion of p-nitrochlorobenzene is 96%. The presence of the formanilide reduces tertiary amine byproduct which becomes excessive in the case of reaction in dimethylformamide, for example.

Provenance & Evidence