Hydrazine hydrate (1:1) → HCID 9856929, compound

HRID 642084Notes

Reaction equation

HRID 642084 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13](OC)=[O:14])=[O:8])=[CH:5][CH:4]=1)#[N:2].O.[NH2:23][NH2:24]>CCO>[C:1]([C:3]1[CH:21]=[CH:20][C:6]([C:7]([NH:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:12]([C:13]([NH:23][NH2:24])=[O:14])[CH:11]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2676472HCID 2676472, compound

Product 1

HCID 9856929HCID 9856929, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl 3-[(4-cyanobenzoyl)amino]benzoate (762 mg, 2.72 mmol) in EtOH (8 mL) was added hydrazine hydrate (1.79 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 mL) and water (3×3 mL) and drying under vacuo at 60° C. for 2 hrs gave 518 mg of the title compound (68%) as a white solid in 98.8% 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 mL) and water (3×3 mL)
  5. customdrying under vacuo at 60° C. for 2 hrs

Sources & evidence

ORD record
ord-51c74f1b232b483e842bf0235bb15fd3
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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