Methanol → Methyl 4-amino-6-chloro-5-fluoropicolinate

HRID 407224Notes

Reaction equation

HRID 407224 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([OH:12])=[O:11])[CH:3]=1.S(Cl)(Cl)=O.[CH3:17]O>O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([O:12][CH3:17])=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 86675406HCID 86675406, compound

Product 1

HCID 86668302Methyl 4-amino-6-chloro-5-fluoropicolinateYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-amino-6-chloro-5-fluoropicolinic acid (23.8 g, 125 mmol) in MeOH (400 ml), cooled in an ice water bath, thionyl chloride (11.78 ml, 162 mmol) was added. The reaction mixture was heated to an internal temperature of 50° C., for 8 hours. The reaction mixture was then diluted with H2O, and extracted with EtOAC (3×100 mL). The combined organics were washed with Sat. NaCl, dried over Mg Sulfate, filtered and concentrated under vacuum to give methyl 4-amino-6-chloro-5-fluoropicolinate (21.9 g, 107 mmol, 86% yield).

Workup

  1. extractionextracted with EtOAC (3×100 mL)
  2. washThe combined organics were washed with Sat. NaCl
  3. dry with materialdried over Mg Sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-900fdc93d6034433a65e442fc56cdd91
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Reaction notes

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