Pyridine → N-(4-Chloro-1,1'-biphenyl-2-yl)acetamide

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.;

1. customthe layers were separated
2. extractionThe aqueous phase was extracted with dichloromethane (3×75 mL)
3. washThe combined organic phase was washed sequentially with a 0.1 N hydrochloric acid solution (2×50 mL)
4. dry with materiala saturated, aqueous sodium bicarbonate solution (50 mL), dried over anhydrous sodium sulfate
5. filtrationfiltered
6. customthe solvent evaporated in vacuo
7. customto yield a brown oil
8. customremoved in vacuo (×3)
9. customto afford a brown solid which

ORD record

ord-05f6ad89d1c84e759caa37baa8fc2bb2

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06894061B2