Pyridine → 2-Methyl-6-pivalamidoisonicotinic acid

HRID 623646Notes

Reaction equation

HRID 623646 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[N:10]=1)[C:5]([OH:7])=[O:6].N1C=CC=CC=1.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([NH:1][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 124040272-Amino-6-methylisonicotinic acid

Product 1

HCID 675100132-Methyl-6-pivalamidoisonicotinic acidYield 179.6%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2-amino-6-methylisonicotinic acid (150 mg, 0.99 mmol) and pyridine (310 mg, 3.9 mmol) in N,N-dimethylformamide (2.0 mL) is added pivaloyl chloride (240 mg, 2.0 mmol) at room temperature. The mixture is stirred overnight at room temperature, and diluted with saturated aqueous citric acid (10 mL). Whole is extracted with ethyl acetate/toluene (2:1, 10 mL×3). Combined organic layers are washed with water, brine, dried over sodium sulfate. The organic solvent is removed under reduced pressure to give 420 mg (quantitative yield) of the titled compound as a white solid.

Workup

  1. extractionWhole is extracted with ethyl acetate/toluene (2:1, 10 mL×3)
  2. washCombined organic layers are washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customThe organic solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-a740f6434f994815b4218bcb5594507d
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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