Acetic Acid → 2-(6-Amino-3-chloropyridin-2-yl)-2-methoxyiminoacetic acid

HRID 1075273Notes

Reaction equation

HRID 1075273 reaction equation
[ClH:1].[NH2:2][C:3]1[N:8]=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=1.C(O)(=O)C.[Cl-]>O>[NH2:2][C:3]1[N:8]=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10]([OH:12])=[O:11])[C:6]([Cl:1])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 312ChlorideHCID 867377252-(6-Aminopyridin-2-yl)-2-methoxyiminoacetic acid hydrochloride

Product 1

HCID 537959242-(6-Amino-3-chloropyridin-2-yl)-2-methoxyiminoacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(6-aminopyridin-2-yl)-2-methoxyiminoacetic acid hydrochloride (syn isomer), acetic acid (350 ml.) and water (10 ml.) was introduced chloride gas for 1.5 hours. After the removal of the excess of the chlorine gas by bubbling air into the reaction mixture, the solvent was distilled off. The residue was pulverized in diethyl ether and collected by filtration. After the addition of water and ethyl acetate to the resultant powder (9.8 g.), the aqueous layer was separated and washed with ethyl acetate. The ethyl acetate layer and washings were combined together, and further extracted with water. The aqueous layers were combined together and adjusted to pH 4 with 1 N aqueous solution of sodium hydroxide, and then the solvent was distilled off under reduced pressure. The remaining water in the residue was azeotropically removed with benzene three times to yield brownish powder which was dried in a desiccator to give 2-(6-amino-3-chloropyridin-2-yl)-2-methoxyiminoacetic acid (syn isomer) (3.27 g.).

Workup

  1. customAfter the removal of the excess of the chlorine gas
  2. customby bubbling air into the reaction mixture
  3. distillationthe solvent was distilled off
  4. filtrationcollected by filtration
  5. additionAfter the addition of water and ethyl acetate to the resultant powder (9.8 g.)
  6. customthe aqueous layer was separated
  7. washwashed with ethyl acetate
  8. extractionfurther extracted with water
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe remaining water in the residue was azeotropically removed with benzene three times
  11. customto yield brownish powder which
  12. customwas dried in a desiccator

Sources & evidence

ORD record
ord-334526b3ccb14b3180c94184b2df965f
Source dataset
uspto-grants-1983_07
Patent number
US04395411

Reaction notes

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