2-Chloropyridine → 2-Pyridinamine, N,N-diphenyl-

A 30 mL of reactor equipped with magnetic stir bar was charged with 33 mg (0.046 mmol) of [(t-Bu)2P(Cl)PdCl2]2, 0.50 g (4.4 mmol) of 2-chloropyridine, 0.70 g (4.14 mmol) of Ph2NH and 0.58 g (5.17 mmol) of KO-t-Bu in 2 mL of toluene. The reaction mixture was refluxed overnight. The reaction mixture was cooled to room temperature, transferred to a separatory funnel, and diluted with 100 mL of diethyl ether and 20 mL of H2O. The layers were separated, and organic layer was washed with H2O (2×50 mL), brine (30 mL), and dried over MgSO4, filtered, and solvents removed from the filtrate by rotary evaporation. The resulting residue was chromatographed on silicon gel. The eluate was concentrated by rotary evaporation followed by high vacuum to give 2-pyridyldiphenylamine. LC-MS Found: 247.3 (M++1).

1. customA 30 mL of reactor equipped with magnetic stir bar
2. temperatureThe reaction mixture was refluxed overnight
3. customtransferred to a separatory funnel
4. customThe layers were separated
5. washorganic layer was washed with H2O (2×50 mL), brine (30 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customsolvents removed from the filtrate by rotary evaporation
9. customThe resulting residue was chromatographed on silicon gel
10. concentrationThe eluate was concentrated by rotary evaporation

ORD record

ord-d6640d8bb9d842b4b042c3825228aec3

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06878850B2