Benzyl 4-(2-hydrazino-2-oxoethoxy)benzoate → 4-(2-Hydrazino-2-oxoethoxy)benzoic acid

HRID 642081

Reaction equation

HRID 642081 reaction equation
[NH:1]([C:3](=[O:22])[CH2:4][O:5][C:6]1[CH:21]=[CH:20][C:9]([C:10]([O:12]CC2C=CC=CC=2)=[O:11])=[CH:8][CH:7]=1)[NH2:2]>CC(O)=O.[Pd]>[NH:1]([C:3](=[O:22])[CH2:4][O:5][C:6]1[CH:21]=[CH:20][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[NH2:2]

Participants

4

Reactant 1

HCID 9922354Benzyl 4-(2-hydrazino-2-oxoethoxy)benzoate

Product 1

HCID 98558384-(2-Hydrazino-2-oxoethoxy)benzoic acidYield 43.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

In an Parr autoclave, a solution of benzyl 4-(2-hydrazino-2-oxoethoxy)benzoate (400 mg, 1.3 mmol) and a catalytic amount Pd/C in AcOH (25 mL) was stirred under hydrogen pressure (5 Bars) at rt for 45 min. After filtration over celite, the filtrate was evaporated off. The residue was taken up in MeOH and a beige solid precipitated out. Filtration and drying under vacuo at 50° C. overnight gave the title compound as a beige solid (118 mg) in a 42% yield.

Workup

  1. filtrationAfter filtration over celite
  2. customthe filtrate was evaporated off
  3. customa beige solid precipitated out
  4. filtrationFiltration
  5. customdrying under vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-7eff46c438b449c48828ec83b8c1e2f2
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Linked notes

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