Sodium Hydroxide → 2-Acetyl-3-pyridinecarboxylic acid

HRID 2372176Notes

Reaction equation

HRID 2372176 reaction equation
[C:1]([C:4]1[N+:12]([O-])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[OH-].[Na+].[H][H]>O.[Pd]>[C:1]([C:4]1[N:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 139287372-acetylnicotinic acid N-oxideHCID 178418361HCID 178418361, compound

Product 1

HCID 101762782-Acetyl-3-pyridinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Sixteen grams (88.4 mmol) of 2-acetylnicotinic acid N-oxide (J. Chem. Soc., 1961, 5216) is added to a solution of sodium hydroxide (3.5 g, 88.4 mmol) in 300 ml of water. The pH is adjusted to 9 by the addition of 6N NaOH, and 10% palladium on carbon (1.6 g) is added. The mixture is then hydrogenated until a 20% excess of hydrogen is taken up. The reaction mixture is filtered through Celite, and the pH of the filtrate is adjusted to 2.5 with 6N HCL. The solvent is removed by rotoevaporation and the residue is taken up in methanol. The mixture is filtered and the filtrate is evaporated to give a pale beige solid, 2-acetylnicotinic acid.

Workup

  1. additionis added
  2. filtrationThe reaction mixture is filtered through Celite
  3. customThe solvent is removed by rotoevaporation
  4. filtrationThe mixture is filtered
  5. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-7f289b956b8743f09e62d918024fbda6
Source dataset
uspto-grants-1992_03
Patent number
US05098462

Reaction notes

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