Sodium Hydroxide → 3-amino-4,5-dichloro-6-ethoxypicolinic Acid

HRID 2407825Notes

Reaction equation

HRID 2407825 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([O:15]C)=[O:14])=[N:4][C:5]([O:10][CH2:11][CH3:12])=[C:6]([Cl:9])[C:7]=1[Cl:8].[OH-].[Na+]>CO>[NH2:1][C:2]1[C:3]([C:13]([OH:15])=[O:14])=[N:4][C:5]([O:10][CH2:11][CH3:12])=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66989872HCID 66989872, compound

Product 1

HCID 669893333-amino-4,5-dichloro-6-ethoxypicolinic AcidYield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the compound prepared in Example 430 (0.025 g) in methanol (1 mL) was treated with sodium hydroxide (0.094 mL) and refluxed for 3 hours. This material was evaporated in vacuo and residue dissolved in water and acidified with 1 mol/L hydrochloric acid. The product was extracted with ethyl acetate, dried, and evaporated in vacuo to provide the title compound (0.011 g) with the following physical data.

Workup

  1. temperaturerefluxed for 3 hours
  2. customThis material was evaporated in vacuo and residue
  3. dissolutiondissolved in water
  4. extractionThe product was extracted with ethyl acetate
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1ccdfec4f33c4dfcb9201186734cdfbe
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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