Methanol → Methyl 6-chloropicolinate

HRID 902013Notes

Reaction equation

HRID 902013 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[N:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][CH:7]=1.[CH3:15]O>C(Cl)(Cl)Cl>[Cl:5][C:6]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 208126-Chloropicolinic acidHCID 24386Thionyl Chloride

Product 1

HCID 242723Methyl 6-chloropicolinateYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Add thionyl chloride (3.7 mL, 50.8 mmol) to a solution of 6-chloropicolinic acid (4.0 g, 25.4 mmol) in methanol (85 mL) at 0° C. Stir the resultant solution for 15 minutes at 0° C., 0.5 hours at room temperature, and 6 hours at 50° C. Concentrate the reaction in vacuo and dilute with CHCl3 (150 mL). Wash the organic solution with saturated aqueous sodium bicarbonate (3×100 mL), and brine (1×100 mL) and dry with sodium sulfate. Filtration and concentration afford methyl 6-chloropicolinate 4.38 g (100%) as a white solid.

Workup

  1. custom0.5 hours
  2. customat room temperature
  3. custom6 hours
  4. customat 50° C
  5. concentrationConcentrate
  6. customthe reaction in vacuo
  7. washWash the organic solution with saturated aqueous sodium bicarbonate (3×100 mL), and brine (1×100 mL)
  8. dry with materialdry with sodium sulfate
  9. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-3f4f58642f634a0b83a02547dc18e714
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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