Hydrazine hydrate (1:1) → HCID 9923619, compound

HRID 642103Notes

Reaction equation

HRID 642103 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([C:7]([NH:9][C:10]2[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][CH:11]=2)=[O:8])=[CH:3][CH:2]=1.O.[NH2:27][NH2:28]>CCO>[NH:27]([C:14]([C:13]1[CH:18]=[CH:19][C:10]([NH:9][C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:2][CH:3]=2)=[O:8])=[CH:11][CH:12]=1)=[O:15])[NH2:28]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2838376HCID 2838376, compound

Product 1

HCID 9923619HCID 9923619, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl 4-[([1,1′-biphenyl]-4-ylcarbonyl)amino]benzoate (880 mg, 2.66 mmol) in EtOH (10 mL) was added hydrazine hydrate (1.8 mL). After stirring for 7 days at reflux, the reaction mixture was cooled to rt and a white solid precipitated out. Filtration, washing with EtOH (3×2 mL) and water (3×2 mL), and drying under vacuo at rt for 6 hrs gave 585 mg of the title compound (66%) as a white solid in 96.4% 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 (3×2 mL) and water (3×2 mL)
  5. customdrying under vacuo at rt for 6 hrs

Sources & evidence

ORD record
ord-392b98687bde47559601684becb0b56e
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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