Methanol → 4-Butyl-1,2-benzenediamine

Participants

Reaction Steps

1.11 g (5.15 mM) of 4-butyl-2-nitroaniline, 5 ml of methanol, 0.35 g of activated carbon and 0.04 gof ferric chloride hexahydrate were placed in a 50 ml-three-neckedflask and kept at about 60° C. To themixture, 1.5 ml (24.7 mM) of hydrazine hydrate wasgradually added dropwise, followed by stirring for 2 hours under heat refluxing. After the reaction, thereaction mixture was subjected to filtration by meansof suction under heating to remove the activatedcarbon. The filtrate was concentrated under reducedpressure and an appropriate amount of water was addedthereto. The mixture was subjected to extraction withethyl acetate. The organic layer was washed withwater and dried with milabilite, followed byconcentration under reduced pressure to obtain a crudeproduct. To the crude product (residue), anappropriate amount of hexane was added, followed bycooling on an ice bath to precipitate a crystal. Thecrystal was recovered by filtration to obtain 0.82 gof 4-butyl-1,2-phenylenediamine (Yield: 87.4%).

Provenance & Evidence