Hydrazine hydrate (1:1) → 2-(Benzyloxy)acetohydrazide

HRID 512004Notes

Reaction equation

HRID 512004 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[NH2:15][NH2:16]>CO>[CH2:6]([O:5][CH2:4][C:3]([NH:15][NH2:16])=[O:2])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11745225Methyl 2-(benzyloxy)acetate

Product 1

HCID 224803422-(Benzyloxy)acetohydrazideYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 70 (2.75 g, 15.3 mmol) in methanol (50 mL) and hydrazine hydrate (65% in water, 2.3 g, 30 mmol) was heated under reflux for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was diluted with benzene. The solvent was evaporated and the crude product was further dried under high vacuum (6 h) to give 71 (2.75 g), as a light yellow waxy material, which was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with benzene
  5. customThe solvent was evaporated
  6. dry with materialthe crude product was further dried under high vacuum (6 h)

Sources & evidence

ORD record
ord-dbf48fcdb80343d89e156c584dfe93e6
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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