4-Aminopyridine → 4-(2,2,2-Trimethylacetamido)pyridine

HRID 2307767Notes

Reaction equation

HRID 2307767 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:8](Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>ClCCl.O>[CH3:10][C:9]([CH3:12])([CH3:11])[C:8]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)=[O:13]

Participants

6

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 4270594-(2,2,2-Trimethylacetamido)pyridineYield 74.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-aminopyridine (10 g, 106 mmol) and pivaloyl chloride (12.9 g, 107 mmol) in 200 mL dichloromethane was cooled to 0° C. and treated slowly with triethylamine (10.9 g, 108 mmol), warmed to room temperature, stirred overnight, and diluted with water. The aqueous layer was extracted three times with dichloromethane and the combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The product was recrystallized from toluene to provide the desired product (14 g, 74%).

Workup

  1. temperaturewarmed to room temperature
  2. extractionThe aqueous layer was extracted three times with dichloromethane
  3. washthe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was recrystallized from toluene

Sources & evidence

ORD record
ord-0f939b85dae645c686b2887498bb41c2
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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