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

HRID 1815672Notes

Reaction equation

HRID 1815672 reaction equation
P(Cl)(C(C)(C)C)C(C)(C)C.Cl[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[NH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O(C(C)(C)C)[K]>C1(C)C=CC=CC=1.C(OCC)C.O>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:18]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 79772-ChloropyridineHCID 11487DiphenylamineHCID 139566Di-tert-butylchlorophosphineHCID 178418922HCID 178418922, compound

Product 1

HCID 121203782-Pyridinamine, N,N-diphenyl-

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A 30 mL of reactor equipped with magnetic stir bar was charged with 50 mg (0.09 mmol) of (t-Bu)2PCl)2PdCl2, 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).

Workup

  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

Sources & evidence

ORD record
ord-ceefede3c60b409d9764e71fe5955ca0
Source dataset
uspto-grants-2005_04
Patent number
US06878850B2

Reaction notes

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