6-Chloropicolinic acid → HCID 62233427, compound

HRID 1769938Notes

Reaction equation

HRID 1769938 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1>S(Cl)(Cl)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH:7][CH2:6][CH2:5][CH3:4])=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 208126-Chloropicolinic acid

Product 1

HCID 62233427HCID 62233427, compoundYield 158.6%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

6-chloropicolinic acid (3 g) and thionyl chloride (50 ml) was refluxed for one hour. The excess thionyl chloride was evaporated in vacuo and dichloromethane added to the residual picolinoyl chloride. This solution was poured into an excess of n-propylamine in dichloromethane. The solution was then washed with water, dried over anhydrous magnesium sulphate and the dichloromethane evaporated to give 6-chloro-2-N-n-propyl pyridine carboxamide (3 g) as a yellow oil.

Workup

  1. customThe excess thionyl chloride was evaporated in vacuo and dichloromethane
  2. additionadded to the residual picolinoyl chloride
  3. additionThis solution was poured into an excess of n-propylamine in dichloromethane
  4. washThe solution was then washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customthe dichloromethane evaporated

Sources & evidence

ORD record
ord-febd20f576fa48e39773efec584b66fb
Source dataset
uspto-grants-1995_01
Patent number
US05384305

Reaction notes

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