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

HRID 642072Notes

Reaction equation

HRID 642072 reaction equation
[CH2:1]([O:7][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][CH3:6].O.[NH2:28][NH2:29]>CCO>[CH2:1]([O:7][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][CH3:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 4933611Methyl 4-{[4-(hexyloxy)benzoyl]amino}benzoate

Product 1

HCID 101328774-(hexyloxy)-N-[4-(hydrazinocarbonyl)phenyl]benzamideYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl 4-{[4-(hexyloxy)benzoyl]amino}benzoate (856 mg, 2.41 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 681 mg of the title compound (80%) as a white solid in 99.7% 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-118a8f56c91c49d78e640cc15d227d8a
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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