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

HRID 1822746Notes

Reaction equation

HRID 1822746 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:15](Cl)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[CH3:17][C:16]([CH3:19])([CH3:18])[C:15]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)=[O:20]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 4270594-(2,2,2-Trimethylacetamido)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 20 g of 4-Aminopyridine and 37 mL of triethylamine in 380 mL of methylene chloride is added 28.8 mL of pivaloyl chloride in a dropwise fashion. After 1 hour at room temperature the reaction mixture is washed with water and sodium bicarbonate solution, dried over magnesium sulfate and the solvent is removed in vacuo. The residue is triturated with hexane to afford 4-trimethylacetamidopyridine as a white solid.

Workup

  1. washAfter 1 hour at room temperature the reaction mixture is washed with water and sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent is removed in vacuo
  4. customThe residue is triturated with hexane

Sources & evidence

ORD record
ord-bf72d98aa8b64a6b9f7ecb5d7393c832
Source dataset
uspto-grants-2006_05
Patent number
US07037922B1

Reaction notes

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