2-Nitroaniline → HCID 19744231, compound

Participants

Reaction Conditions

Reaction Steps

5.6 Grams of 5-chloro-2-nitro-4-(1',1',2',2'-tetrafluoroethoxy)aniline [i.e. the o-nitroaniline compound (VI) containing chlorine as the substituent X] was dissolved in a mixed solvent of 25 ml of ethyl acetate and 25 ml of acetic acid. The resulting solution was dropwise added to a suspension of 4.7 g of iron powders in a mixed solution of 5 ml of acetic acid and 50 ml of water while maintaining the temperature at 50° C. Thereafter, stirring was continued for 20 minutes at 50° C. to 60° C. The reaction solution was filtered through Celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and water in this order, dried over anhydrous magnesium sulfate and concentrated. The residue obtained was subjected to column chromatography on silica gel with chloroform and ethyl acetate as eluents to obtain 5.2 g of 4-chloro-5-(1',1',2',2'-tetrafluoroethoxy)-1,2-benzenediamine [i.e. the o-phenylenediamine compound (IV) containing chlorine as the substituent X]. 1H-NMR (CDCl3): δ(ppm) 6.65-6.75(2H), 5.95(1H, tt, J=53, 3 Hz), 3.40(4H, s, broad)

Provenance & Evidence