Sodium Sulfite → 6-Methoxynicotinic acid

HRID 324516Notes

Reaction equation

HRID 324516 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][CH:4]=1.[Mn]([O-])(=O)(=O)=[O:12].[K+].S([O-])([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.O>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]([OH:12])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 33645766-Methoxypyridine-3-carbaldehyde

Product 1

HCID 5924996-Methoxynicotinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 6-methoxy-3-pyridinecarboxaldehyde (50 mg, 0.36 mmol; prepared according to the method of Comins and Killpack, J. Org. Chem., 1990, 55, 69-73) in t-butanol (0.5 ml) was added a solution of potassium permanganate (81 mg) in water (1.0 ml). The mixture was stirred at room temperature for two hours, and then saturated sodium sulphite solution was added until the purple colour disappeared. Reaction mixture was extracted with chloroform several times as it was gradually acidified with dilute HCl (2N). Chloroform extracts were concentrated in vacuo to yield the title compound (42 mg) as a white solid.

Workup

  1. customprepared
  2. customReaction mixture
  3. extractionwas extracted with chloroform several times as it
  4. concentrationChloroform extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-609ffab1efe6406692f63a5091ffb537
Source dataset
uspto-grants-2001_04
Patent number
US06218393B1

Reaction notes

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