Hydrazine hydrate (1:1) → HCID 9966612, compound

HRID 642127Notes

Reaction equation

HRID 642127 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([O-])=[O:16])=[CH:13][CH:12]=1)=[O:8])([O-:3])=[O:2].O.[NH2:24][NH2:25]>CCO>[NH:24]([C:15]([C:14]1[CH:18]=[CH:19][C:11]([CH2:10][NH:9][C:7](=[O:8])[C:6]2[CH:20]=[CH:21][CH:22]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:12][CH:13]=1)=[O:16])[NH2:25]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 25706302HCID 25706302, compound

Product 1

HCID 9966612HCID 9966612, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-{[(3-nitrobenzoyl)amino]methyl}benzoate (500 mg, 1.59 mmol) in EtOH (6 mL) was added hydrazine hydrate (1.16 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 (2×2 mL), EtOH/water (2×2 mL)and water (2×2 mL), and drying under vacuo at 70° C. for 5 hrs gave 379 mg of the title compound (76%) as a pale yellow 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 EtOH (2×2 mL), EtOH/water (2×2 mL)and water (2×2 mL)
  5. customdrying under vacuo at 70° C. for 5 hrs

Sources & evidence

ORD record
ord-348b23b1b394458582e6386dc8a38252
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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