Water → HCID 9878958, compound

HRID 642098Notes

Reaction equation

HRID 642098 reaction equation
[O:1]([CH2:8][C:9]([NH:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:23][NH2:24].O>CCO>[NH:23]([C:16]([C:15]1[CH:20]=[CH:21][C:12]([NH:11][C:9](=[O:10])[CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:14]=1)=[O:17])[NH2:24]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 674765HCID 674765, compound

Product 1

HCID 9878958HCID 9878958, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl 4-[(phenoxyacetyl)amino]benzoate (843 mg, 2.95 mmol) in EtOH (10 mL) was added hydrazine hydrate (2.15 mL). After stirring for 15 hrs at reflux, the reaction mixture was cooled to rt. Water (10 mL) was added to the reaction mixture and a white solid precipitated out. Filtration, washing with EtOH/water (2×2 mL) and water (3×1 mL), and drying under vacuo at 70° C. for 6 hrs gave 389 mg of the title compound (46%) as a white solid in 95.4% 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/water (2×2 mL) and water (3×1 mL)
  5. customdrying under vacuo at 70° C. for 6 hrs

Sources & evidence

ORD record
ord-f65e0f7b19d04c81b4b6d186e249c5da
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

Loading…