(4-Chlorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanone → {2-[(3-Aminopyridin-2-yl)amino]phenyl}(4-chlorophenyl)methanone

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Reaction Steps

Under an atmosphere of nitrogen, 29 g (0.187 mole) of titanium trichloride was added portionwise (cautiously; in hood) to 200 g of ice and the resulting solution was diluted to 250 ml volume with water. This was added, all at once, at 30° C. to a stirred solution of 11.0 g (0.0312 mole) of (4-chlorophenyl)[2-[(3-nitro-2-pyridinyl)amino]phenyl]methanone, 300 ml of ethyl acetate: methanol (1:1), 100 ml of acetic acid: water (1:1) and 20 ml more solution of titanium trichloride. The reaction mixture was stirred for 20 min then diluted with one liter of water and filtered. The filter cake was washed with water and then partitioned between 200 ml of methylene chloride and 75 ml of 10% aqueous sodium hydroxide solution. The methylene chloride layer was washed with 75 ml of water, dried over sodium sulfate and concentrated in vacuo. The residue (7 g) was recrystallized from ethyl acetate-isopropyl ether to give 6.0 g of gold solid, m.p. 145°-146° C.

Provenance & Evidence