5-chloro-2-phenylaniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 4-chloro-1,1′-biphenyl-2-ylamine (3.46 g, 17.0 mmol) in dichloromethane (8.5 mL) was treated with pyridine (3.2 mL, 39 mmol), acetic anhydride (1.77 mL, 18.7 mmol), and 4-(dimethylamino)pyridine (0.62 g, 0.51 mmol) and stirred at room temperature for 12 hours. A saturated, aqueous solution of ammonium chloride (150 mL) was added, and the layers were separated. The aqueous phase was extracted with dichloromethane (3×75 mL). The combined organic phase was washed sequentially with a 0.1 N hydrochloric acid solution (2×50 mL) and a saturated, aqueous sodium bicarbonate solution (50 mL), dried over anhydrous sodium sulfate, filtered and the solvent evaporated in vacuo to yield a brown oil. Toluene was added and removed in vacuo (×3) to afford a brown solid which, upon trituration with ethyl acetate/hexane, afforded the title compound as a homogeneous, colorless, crystalline solid (2.28 g, 93%), m.p. 125-127° C.; the layers were separated The aqueous phase was extracted with dichloromethane (3×75 mL) The combined organic phase was washed sequentially with a 0.1 N hydrochloric acid solution (2×50 mL) a saturated, aqueous sodium bicarbonate solution (50 mL), dried over anhydrous sodium sulfate filtered the solvent evaporated in vacuo to yield a brown oil removed in vacuo (×3) to afford a brown solid which