Triethylamine → 2-(Pivaloylamino)pyridine

HRID 557254Notes

Reaction equation

HRID 557254 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:15](Cl)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CO>[CH3:17][C:16]([CH3:19])([CH3:18])[C:15]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 11430Potassium CarbonateHCID 62493Pivaloyl chloride

Product 1

HCID 10515192-(Pivaloylamino)pyridineYield 84.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-aminopyridine (50.0 g, 531 mmol) in methylene chloride (500 mL) were added triethylamine (81.4 mL, 584 mmol) and pivaloyl chloride (71.9 mL, 584 mmol) at 0° C, which was stirred at room temperature for 4 hours 30 minutes. The reaction solution was partitioned in water and methylene chloride. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous magnesium sulfate, and the solvent thereof was evaporated under a reduced pressure. To a solution of the resulting residue in methanol (300 mL) was added potassium carbonate (73.4 g, 531 mmol) at 0° C, which was stirred at room temperature for 90 minutes. The reaction solution was partitioned into water and ethyl acetate at room temperature. The organic layer was washed with saturated sodium chloride water, dried over anhydrous magnesium sulfate, and the solvent thereof was evaporated under a reduced pressure. To the residue was added heptane (300 mL), and the deposited solid was recovered by filtration to obtain title compound (80.2 g). Furthermore, the filtrate was concentrated under a reduced pressure, the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (12.2 g).

Workup

  1. customThe reaction solution was partitioned in water
  2. washThe organic layer was washed with water and saturated sodium chloride water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent thereof was evaporated under a reduced pressure
  5. stirringwhich was stirred at room temperature for 90 minutes
  6. customThe reaction solution was partitioned into water and ethyl acetate at room temperature
  7. washThe organic layer was washed with saturated sodium chloride water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent thereof was evaporated under a reduced pressure
  10. additionTo the residue was added heptane (300 mL)
  11. filtrationthe deposited solid was recovered by filtration

Sources & evidence

ORD record
ord-b2c21a55adbd442690b9675a7a08c53a
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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