Methyl Anthranilate → 2-Aminobenzohydroxamic acid

HRID 235911Notes

Reaction equation

HRID 235911 reaction equation
[OH-:1].[Na+].[NH2:3]O.Cl.[C:6]([O:15]C)(=O)[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH2:9]>O>[OH:1][NH:3][C:6](=[O:15])[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH2:9]

Participants

5

Reactant 3

HCID 8635Methyl AnthranilateHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 797212-Aminobenzohydroxamic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

48 parts of NaOH are introduced into 300 parts of water. 41.6 parts of NH2OH.HCl are added in portions, with cooling, followed by 45.2 parts of methyl anthranilate. After the mixture has been left to stand at room temperature for 3 days, the solution is concentrated and concentrated hydrochloric acid is added to the residue thus obtained until the pH is 6. After the mixture has been filtered and the filtrate has been washed with ethanol, anthranilic acid hydroxylamide is obtained as colourless crystals of melting point 140°-142° C. with a yield of 85%.

Workup

  1. temperaturewith cooling
  2. waitAfter the mixture has been left
  3. concentrationthe solution is concentrated
  4. additionconcentrated hydrochloric acid is added to the residue
  5. customthus obtained until the pH is 6
  6. filtrationAfter the mixture has been filtered
  7. washthe filtrate has been washed with ethanol

Sources & evidence

ORD record
ord-e53a201a113545f09153d46d703ed5a9
Source dataset
uspto-grants-1987_02
Patent number
US04642322

Reaction notes

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