Hydrochloric Acid → 4-Amino-5,6-dichloropicolinic Acid

HRID 2407809Notes

Reaction equation

HRID 2407809 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([O:12]C)=[O:11])[CH:3]=1.C[Si](C)(C)[O-].[K+].Cl.C(OCC)(=O)C>O1CCCC1.O>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([OH:12])=[O:11])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23668039Potassium trimethylsilanolateHCID 58504072Methyl 4-amino-5,6-dichloro-2-pyridinecarboxylate

Product 1

HCID 585040704-Amino-5,6-dichloropicolinic AcidYield 98.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound prepared in Example 405 (2.438 g) and potassium trimethylsilanolate (2.971 g) were suspended in tetrahydrofuran (100 mL) and stirred at reflux for 4 hours. The reaction mixture was dissolved in water and added to 1 N hydrochloric acid. Ethyl acetate was added and the system stirred at room temperature. The organics were dried, magnesium sulfate and concentrated under reduced pressure to furnish the title compound (2.250 g), which was used without further purification, possessing the following physical data.

Workup

  1. temperatureat reflux for 4 hours
  2. stirringthe system stirred at room temperature
  3. customThe organics were dried
  4. concentrationmagnesium sulfate and concentrated under reduced pressure

Sources & evidence

ORD record
ord-2d3e1c67be8e44c29e6804966f15762b
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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