Potassium Hydroxide → Isothiazolo[5,4-b]pyridine-3-carboxylic acid

HRID 2390937Notes

Reaction equation

HRID 2390937 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[OH-:7].[K+].[S:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[C:11]([CH2:18][OH:19])=[N:10]1>O>[S:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[C:11]([C:18]([OH:7])=[O:19])=[N:10]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 66702998HCID 66702998, compound

Product 1

HCID 66702565Isothiazolo[5,4-b]pyridine-3-carboxylic acidYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium permanganate (2.25 mmol) and potassium hydroxide (1.79 mmol) were added to a solution of isothiazolo[5,4-b]pyridin-3-ylmethanol (1.08 mmol) in water (4 mL) and the resulting solution was allowed to react for 3 h at rt. The reaction mixture was filtered through Celite and was extracted with ethyl acetate (3×10 mL). The pH of the combined aqueous layers was adjusted to 2 by the addition of 0.6 M hydrochloric acid. The slurry was stirred for 5 min and the solids were collected by filtration to provide isothiazolo[5,4-b]pyridine-3-carboxylic acid in 42% yield as a light yellow solid.

Workup

  1. customto react for 3 h at rt
  2. filtrationThe reaction mixture was filtered through Celite
  3. extractionwas extracted with ethyl acetate (3×10 mL)
  4. additionThe pH of the combined aqueous layers was adjusted to 2 by the addition of 0.6 M hydrochloric acid
  5. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-58998398ef134bae95f81e3673a0d3c1
Source dataset
uspto-grants-2012_09
Patent number
US08273891B2

Reaction notes

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