HCID 86622289, compound → HCID 86622288, compound

Participants

Reaction Steps

To a solution of 2 g of 4-amino-3-nitrophenyl 2,6-dichlorobenzenesulfonate in 85 cm3 of methanol and 33 cm3 of pure acetic acid are added 2.25 g of iron powder. The reaction medium is refluxed for three hours. The insoluble material is filtered off and washed with three times 10 cm3 of preheated methanol. The filtrate is evaporated to dryness under reduced pressure (2 kPa) at a bath temperature of 50° C. The residue is taken up in 50 cm3 of water and then brought to pH 8-9 with sodium hydrogen carbonate and extracted with five times 80 cm3 of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure (2 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/methanol (98/2 by volume)], 900 mg of 3,4-diaminophenyl 2,6-dichlorobenzenesulfonate are obtained in the form of orange crystals, the characteristics of which are as follows:

Provenance & Evidence