Water → 2-(Pivaloylamino)pyridine

HRID 2079996Notes

Reaction equation

HRID 2079996 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:15][C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18].O>ClCCl>[CH3:15][C:16]([CH3:21])([CH3:20])[C:17]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 104392-AminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 10515192-(Pivaloylamino)pyridineYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Aminopyridine (3.1 g, 33 mmol) and triethylamine(6.9 mL, 49 mmol) was dissolved in dichloromethane (40 mL), 2,2-dimethylpropionyl chloride (4.5 mL, 36 mmol) was added on an ice bath, and the solution was stirred for 2 hours at the same temperature. Water was added thereto for extraction, the organic layer was sequentially washed with an aqueous solution of saturated sodium bicarbonate and brine, then, dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, and the title compound (6.0 g, 34 mmol, 102%) was obtained as a white solid.

Workup

  1. extractionfor extraction
  2. washthe organic layer was sequentially washed with an aqueous solution of saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5c8563c29522469ab28974de16e979da
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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