1-Chloro-2,4-Dinitrobenzene → 4-Chloro-M-phenylenediamine

Participants

Reaction Steps

A mixture of 1-chloro-2,4-dinitrobenzene (40.0 g, 0.197 mole), methanol (100 g), and 3.0 g of modified Raney nickel catalyst consisting of about 83.1% Ni, 9.3% Co, 7.1% Al and 0.5% Mo was charged into an autoclave. The autoclave was sealed, pressurized with hydrogen to 700 psig, and the hydrogenation carried out at about 30° C. Hydrogen uptake was observed by monitoring the pressure change. After the hydrogen uptake ceased (approximately 6.0 hrs.), the reaction mixture was heated for a short time longer and then the autoclave was vented. A sample of the reaction mixture was taken and analyzed by liquid chromatography after being separated from the solid catalyst. The desired product 1-chloro-2,4-diaminobenzene was formed in high yield and good purity. Liquid chromatography indicated an area % of 92.4% (excluding the methanol solvent) for the product. Very little dechlorination had occurred.

Provenance & Evidence