Stannous Chloride → N,N-dimethyl-m-phenylenediamine

Participants

Reaction Steps

N,N-dimethyl-3-nitroaniline (3.00 g, 18.1 mmol) was dissolved in ethanol (40 cm3). Tin dichloride (16.3 g, 72.0 mmol) was added and the reaction heated under reflux for 16 h. The reaction mixture was allowed to cool before the bulk of the solvent was removed under reduced pressure. The remaining residue was poured in to water (100 cm3), and basified with sodium hydroxide (3M). The mixture was extracted with chloroform (3×30 cm3). The combined extracts were dried over sodium sulphate, filtered and the solvent removed under reduced pressure to give the product as a brown oil (2.01 g, 82%).

Provenance & Evidence