Dichloromethane → 2-(Pivaloylamino)pyridine

HRID 1927209Notes

Reaction equation

HRID 1927209 reaction equation
C(Cl)Cl.[NH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>O>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:23]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 104392-AminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 10515192-(Pivaloylamino)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a methylene chloride (500 mL) solution of 2-aminopyridine (50 g) were added triethylamine (81 mL) and pivaloyl chloride (72 mL) at 0° C., which was stirred for 4 hours and 30 minutes at room temperature. Water was added to the reaction solution, and then extraction was performed with methylene chloride. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under a reduced pressure. Potassium carbonate (73 g) was added at 0° C. to a methanol (300 mL) solution of the residue thus obtained, which was stirred for 90 minutes at room temperature. Water was added to the reaction solution, and then extraction was performed with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and filtered, after which the filtrate was concentrated under a reduced pressure. Heptane (300 mL) was added to the residue, and the precipitated solids were filtered off to obtain the titled compound (80 g). The filtrate was then further concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the titled compound (12 g).

Workup

  1. extractionextraction
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. additionPotassium carbonate (73 g) was added at 0° C. to a methanol (300 mL) solution of the residue
  7. customthus obtained
  8. stirringwhich was stirred for 90 minutes at room temperature
  9. extractionextraction
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationafter which the filtrate was concentrated under a reduced pressure
  14. additionHeptane (300 mL) was added to the residue
  15. filtrationthe precipitated solids were filtered off

Sources & evidence

ORD record
ord-52687dea811841eead96f6269fb11ea6
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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