Methyl 4-amino-3-chloro-5-methoxyiminomethylbenzoate → 4-Amino-3-chloro-5-methoxyiminomethylbenzoic acid

HRID 583146Notes

Reaction equation

HRID 583146 reaction equation
[NH2:1][C:2]1[C:11]([CH:12]=[N:13][O:14][CH3:15])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[Cl:16]>CO.[OH-].[Na+]>[NH2:1][C:2]1[C:11]([CH:12]=[N:13][O:14][CH3:15])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:16]

Participants

4

Reactant 1

HCID 53973576Methyl 4-amino-3-chloro-5-methoxyiminomethylbenzoate

Product 1

HCID 540991344-Amino-3-chloro-5-methoxyiminomethylbenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The methyl 4-amino-3-chloro-5-methoxyiminomethylbenzoate made in the previous step was dissolved in a mixture of 25 ml of methanol and 8 g ml of 10% of aqueous sodium hydroxide and the solution was then was refluxed for 2 hours. The methanol was removed using a rotary evaporator and the residue was partitioned between 25 ml of water and 25 ml of methylene chloride. To the cooled aqueous layer was added 6N aqueous hydrochloric acid, dropwise, with stirring, until the pH of mixture reached a value of 1. The resulting solid was filtered and dried yielding 1.4 g 4-amino-3-chloro-5-methoxyiminomethylbenzoic acid used without further purification.

Workup

  1. temperaturethe solution was then was refluxed for 2 hours
  2. customThe methanol was removed
  3. customa rotary evaporator
  4. customthe residue was partitioned between 25 ml of water and 25 ml of methylene chloride
  5. additionTo the cooled aqueous layer was added 6N aqueous hydrochloric acid
  6. filtrationThe resulting solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-ce22cb967ea3459791869d17268ae29c
Source dataset
uspto-grants-1999_07
Patent number
US05929098

Reaction notes

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