Hydrazine hydrate (1:1) → 3,5-Difluorophenylhydroxyacetohydrazide

HRID 1037751Notes

Reaction equation

HRID 1037751 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:14])[C:10](OC)=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.O.[NH2:16][NH2:17]>CC(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:14])[C:10]([NH:16][NH2:17])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22312159Methyl 2-(3,5-difluorophenyl)-2-hydroxyacetate

Product 1

HCID 698094903,5-Difluorophenylhydroxyacetohydrazide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5.0 g of methyl 3,5-difluorophenylhydroxyacetate (C2) are dissolved in 45.0 ml of 2-propanol. 1.32 ml of hydrazine hydrate are then added dropwise, and the reaction mixture is kept under reflux for 18 hours. The solution is subsequently evaporated to dryness, and the resultant residue is purified by flash chromatography on silica gel (gradient for elution: ethyl acetate/0-20.0% by vol. of methanol), giving 3.70 g of the title compound as colourless solid having a melting point of 119.3° C. (MS: 202.8 (MH+)).

Workup

  1. temperatureunder reflux for 18 hours
  2. customThe solution is subsequently evaporated to dryness
  3. customthe resultant residue is purified by flash chromatography on silica gel (gradient for elution: ethyl acetate/0-20.0% by vol. of methanol)

Sources & evidence

ORD record
ord-6c9a7b06ef9a497d8312c309b2e18cad
Source dataset
uspto-grants-2013_10
Patent number
US08546613B2

Reaction notes

Loading…