Hydrazine hydrate (1:1) → Benzyl 4-(2-hydrazino-2-oxoethoxy)benzoate

HRID 642062Notes

Reaction equation

HRID 642062 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:21]=[CH:20][C:9]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[CH:8][CH:7]=1.O.[NH2:24][NH2:25]>CO>[NH:24]([C:3](=[O:2])[CH2:4][O:5][C:6]1[CH:21]=[CH:20][C:9]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[CH:8][CH:7]=1)[NH2:25]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18381591HCID 18381591, compound

Product 1

HCID 9922354Benzyl 4-(2-hydrazino-2-oxoethoxy)benzoateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of benzyl 4-(2-methoxy-2-oxoethoxy)benzoate (1.0 g, 3.33 mmol) in MeOH (15 mL) was added hydrazine hydrate (1.7 mL). After stirring for 1 h at rt, the reaction mixture was filtered. The cake was washed with MeOH (3×4 mL) and dryed under vacuo at 50° C. overnight gave 936 mg of the title compound (94%) as a white solid in 99.7% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washThe cake was washed with MeOH (3×4 mL)
  3. waitdryed under vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-c207e8783b46446387313d1a5d351b50
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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