Sodium Hydroxide → 3-amino-4-chloro-6-ethoxypicolinic Acid

HRID 2407823Notes

Reaction equation

HRID 2407823 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([O:14]C)=[O:13])=[N:4][C:5]([O:9][CH2:10][CH3:11])=[CH:6][C:7]=1[Cl:8].[OH-].[Na+]>CO>[NH2:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[N:4][C:5]([O:9][CH2:10][CH3:11])=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66990431HCID 66990431, compound

Product 1

HCID 669900813-amino-4-chloro-6-ethoxypicolinic AcidYield 12.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the compound prepared in Example 427 (0.025 g) in methanol (1 mL) was treated with sodium hydroxide (0.11 mL) and refluxed for 18 hours. This material was evaporated in vacuo and residue dissolved in water and acidified with 1N hydrochloric acid. The product was extracted with ethyl acetate, dried, and evaporated in vacuo to provide the title compound (0.003 g) having the following physical data.

Workup

  1. temperaturerefluxed for 18 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-b8f85d303a1d43e983b6315e509a38f4
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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