Sodium Hydroxide → 4-Amino-6-bromo-5-chloro-3-methoxypyridine-2-carboxylic acid

HRID 378793Notes

Reaction equation

HRID 378793 reaction equation
C[O:2][C:3]([C:5]1[C:10]([O:11][CH3:12])=[C:9]([NH2:13])[C:8]([Cl:14])=[C:7]([Br:15])[N:6]=1)=[O:4].[OH-].[Na+]>CO>[NH2:13][C:9]1[C:8]([Cl:14])=[C:7]([Br:15])[N:6]=[C:5]([C:3]([OH:4])=[O:2])[C:10]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21696662Methyl 4-amino-6-bromo-5-chloro-3-methoxypicolinate

Product 1

HCID 216966744-Amino-6-bromo-5-chloro-3-methoxypyridine-2-carboxylic acidYield 80.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl-4-amino-6-bromo-5-chloro-3-methoxypyridine-2-carboxylate (0.300 g, 1.02 mmol) in 10 mL of methanol was added 1 N NaOH (1.10 mL, 1.10 mmol). The reaction mixture was stirred at room temperature for 4 hr and was then concentrated to dryness in vacuo. The resulting aqueous layer was acidified with concentrated HCl. The white solid was collected by filtration and was rinsed with H2O. The solid was dried at 50° C. under vacuum to give 0.230 g of a white fluffy solid; mp 154-156° C.

Workup

  1. concentrationwas then concentrated to dryness in vacuo
  2. filtrationThe white solid was collected by filtration
  3. washwas rinsed with H2O
  4. customThe solid was dried at 50° C. under vacuum

Sources & evidence

ORD record
ord-77b13e98a50846559104d8f1cbe2e628
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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