Triethylamine → 2-(Pivaloylamino)pyridine

HRID 365349Notes

Reaction equation

HRID 365349 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C(N(CC)CC)C>ClCCl>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 10515192-(Pivaloylamino)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.1 equivalents of pivalic acid chloride dissolved in 100 ml of dichloromethane are added dropwise at 0° C. to a solution containing one equivalent of 2-aminopyridine and 1.25 equivalents of triethylamine in 400 ml of dichloromethane. Once the addition is complete, the reaction mixture is brought to room temperature for three hours, and then the reaction mixture is washed with a saturated NaHCO3 solution. After drying of the organic phase, filtration and concentration under reduced pressure, the resulting residue is crystallised from hexane, enabling the expected product to be isolated by filtration.

Workup

  1. additionare added dropwise at 0° C. to a solution
  2. additionOnce the addition
  3. washthe reaction mixture is washed with a saturated NaHCO3 solution
  4. customAfter drying of the organic phase, filtration and concentration under reduced pressure
  5. customthe resulting residue is crystallised from hexane
  6. customto be isolated by filtration

Sources & evidence

ORD record
ord-fbe15bd0863943bc870ad837900d4d26
Source dataset
uspto-grants-2000_10
Patent number
US06127369

Reaction notes

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