Hydrazine hydrate (1:1) → HCID 9879898, compound

HRID 642115Notes

Reaction equation

HRID 642115 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].O.[NH2:25][NH2:26]>CCO>[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([NH:25][NH2:26])=[O:19])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 44515467HCID 44515467, compound

Product 1

HCID 9879898HCID 9879898, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl 4-{[3-(3,4-dihydroxyphenyl)propanoyl]amino}benzoate (227 mg, 0.72 mmol) in EtOH (3.5 mL) was added hydrazine hydrate (0.55 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 (2×1 mL) and water (3×1 mL) and drying under vacuo at 70° C. for 2 hrs gave 117 mg of the title compound (52%) as a white solid in 99.6% 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 (2×1 mL) and water (3×1 mL)
  5. customdrying under vacuo at 70° C. for 2 hrs

Sources & evidence

ORD record
ord-355d2ce887594c1082f1e1dc44a9ce82
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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