Hydrazine hydrate (1:1) → 4-chloro-N-[4-(hydrazinocarbonyl)benzyl]benzamide

HRID 642091

Reaction equation

HRID 642091 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.O.[NH2:23][NH2:24]>CCO>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([NH:23][NH2:24])=[O:15])=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 60409609Methyl 4-{[(4-chlorobenzoyl)amino]methyl}benzoate

Product 1

HCID 98576094-chloro-N-[4-(hydrazinocarbonyl)benzyl]benzamideYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl 4-{[(4-chlorobenzoyl)amino]methyl}benzoate (303 mg, 1.0 mmol) in EtOH (6 mL) was added hydrazine hydrate (1.0 mL). After stirring for 15 h at reflux, the reaction mixture was cooled to rt and a white solid precipitated out. Filtration, washing with water (3×2 mL) and drying under vacuo at 60° C. for 2 hrs gave 213 mg of the title compound (70%) as a white solid in 96.5% 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 water (3×2 mL)
  5. customdrying under vacuo at 60° C. for 2 hrs

Sources & evidence

ORD record
ord-94e1733759f545ac9f483a6d1b5b6b42
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Linked notes

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