2-Nitroaniline → HCID 19744226, compound

Participants

Reaction Conditions

Reaction Steps

4.7 Grams of 5-fluoro-2-nitro-4-(1',1',2',2'-tetrafluoroethoxy)aniline [i.e. the o-nitroaniline compound (VI) containing fluorine as the substituent X] was dissolved in a mixed solvent of 15 ml of ethyl acetate and 15 ml of acetic acid. The resulting solution was dropwise added to a suspension of 4.8 g of iron powders in a mixed solution of 3 ml of acetic acid and 30 ml of water while maintaining the temperature at 40° C. Thereafter, stirring was continued for 15 minutes at 40° C. to 50° 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 as an eluent to obtain 3.9 g of 4-fluoro-5-(1',1',2',2'-tetrafluoroethoxy)-1,2-benzenediamine [i.e. the o-phenylenediamine compound (IV) containing fluorine as the substituent X]. 1H-NMR (CDCl3): δppm 6.40-6.70(2H), 5.90(1H, tt, J=54, 3 Hz), 3.30(4H, broad).

Provenance & Evidence