Water → 5-Chloro-2-picolinic acid

HRID 1769276Notes

Reaction equation

HRID 1769276 reaction equation
C[Si](C)(C)C#[C:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][N:6]=1.S([O-])(OCCCCCCCCCCCC)(=O)=[O:15].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].S(=O)(O)[O-].[Na+].[OH2:43]>>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:15])=[O:43])=[N:6][CH:7]=1

Participants

6

Reactant 5

HCID 962WaterHCID 516875Potassium PermanganateHCID 3423265Sodium Lauryl SulfateHCID 10943735HCID 10943735, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 27628725-Chloro-2-picolinic acid

Procedure

0.10 g (0.5 mmol) of 2-trimethylsilylethynyl-5-chloropyridine, 0.01 g of sodium lauryl sulphate and 2 ml of deionized water are placed under an inert gas atmosphere. Subsequently, 0.25 g (15 mmol) of potassium permanganate is added thereto at 23° while stirring. After 2 hours the reaction mixture is treated with aqueous sodium bisulphite solution (about 40 percent) until, after filtration of a sample over filter paper, the violet colour of the permanganate has disappeared. The suspension is filtered over a layer of Dicalite and the filtrate is adjusted to pH 3 with 1N aqueous hydrochloric acid, whereby a white suspension results. This is cooled in an ice bath and the crystals are filtered off. The crystals are treated with 1 ml of deionized water, the suspension is again cooled to 0° and the crystals are filtered off. These are evaporated twice from methanol/toluene under reduced pressure and the residue is dried in a high vacuum. There are obtained 17 mg of 5-chloropyridine-2-carboxylic acid as a white, solid residue, m.p. 171°-172°.

Workup

  1. filtrationafter filtration of a sample
  2. filtrationover filter paper
  3. filtrationThe suspension is filtered over a layer of Dicalite
  4. customresults
  5. temperatureThis is cooled in an ice bath
  6. filtrationthe crystals are filtered off
  7. additionThe crystals are treated with 1 ml of deionized water
  8. temperaturethe suspension is again cooled to 0°
  9. filtrationthe crystals are filtered off
  10. customThese are evaporated twice from methanol/toluene under reduced pressure
  11. customthe residue is dried in a high vacuum

Sources & evidence

ORD record
ord-1719cc268d284cecb1e542e7eed907d9
Source dataset
uspto-grants-1995_01
Patent number
US05380861

Reaction notes

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