Acetic Acid → 4-{[4-(Hydrazinocarbonyl)benzoyl]amino}benzoic acid

HRID 642112Notes

Reaction equation

HRID 642112 reaction equation
C[O:2][C:3]([C:5]1[CH:22]=[CH:21][C:8]([C:9]([NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)=O.O.[NH2:24][NH2:25].CC(O)=O>CCO.O>[NH:24]([C:3]([C:5]1[CH:22]=[CH:21][C:8]([C:9]([NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)=[O:2])[NH2:25]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 18405738HCID 18405738, compound

Product 1

HCID 98574564-{[4-(Hydrazinocarbonyl)benzoyl]amino}benzoic acidYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 4-{[4-(methoxycarbonyl)benzoyl]amino}benzoic acid (300 mg g, 1 mmol) in EtOH (4.5 mL) was added hydrazine hydrate (0.73 mL). After stirring for 15 h at reflux, the reaction mixture was cooled to rt and a white solid precipitated out. Filtration, washing with EtOH (3×1 mL) and drying under vacuo at 70° C. for 2 hrs gave a white solid. This residue was taken up in water (25 mL) and AcOH (5 mL) was added. A white solid precipitated out which was further washed with water (3×2 mL). Drying at 80° C. for 1 hr gave 220 mg of the title compound (73%) as a white solid in 91.2% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. temperatureat reflux
  2. customa white solid precipitated out
  3. filtrationFiltration
  4. washwashing with EtOH (3×1 mL)
  5. customdrying under vacuo at 70° C. for 2 hrs
  6. customgave a white solid
  7. customA white solid precipitated out which
  8. washwas further washed with water (3×2 mL)
  9. customDrying at 80° C. for 1 hr

Sources & evidence

ORD record
ord-53bb81dd9e00477c817d160a877331b9
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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