Hydrazine hydrate (1:1) → 4-heptyl-N-[4-(hydrazinocarbonyl)phenyl]benzamide

HRID 642075Notes

Reaction equation

HRID 642075 reaction equation
[CH2:1]([C:8]1[CH:26]=[CH:25][C:11]([C:12]([NH:14][C:15]2[CH:24]=[CH:23][C:18]([C:19](OC)=[O:20])=[CH:17][CH:16]=2)=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].O.[NH2:28][NH2:29]>CCO>[CH2:1]([C:8]1[CH:26]=[CH:25][C:11]([C:12]([NH:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([NH:28][NH2:29])=[O:20])=[CH:17][CH:16]=2)=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68409708HCID 68409708, compound

Product 1

HCID 101327784-heptyl-N-[4-(hydrazinocarbonyl)phenyl]benzamideYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl 4-[(4-heptylbenzoyl)amino]benzoate (823 mg, 2.33 mmol) in EtOH (10 mL) was added hydrazine hydrate (1.8 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 (1×2 mL) and water (2×2 mL), and drying under vacuo at rt for 72 hrs gave 619 mg of the title compound (75%) as a white solid in 99.4% 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 (1×2 mL) and water (2×2 mL)
  5. customdrying under vacuo at rt for 72 hrs

Sources & evidence

ORD record
ord-8bac081eb9e24d70aa9fc0247a8e5782
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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