Acetic Acid → 2-Nitroacetophenone hydrazone

HRID 1773764Notes

Reaction equation

HRID 1773764 reaction equation
[N+:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O)([O-:3])=[O:2].O.[NH2:14][NH2:15].C(O)(=O)C>C(O)C>[N+:1]([CH2:4][C:5](=[N:14][NH2:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 948332-Nitro-1-phenylethanone

Product 1

HCID 866578932-Nitroacetophenone hydrazoneYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-nitroacetophenone (12.28 g, 0.074 mol) in ethanol (100 mL) was treated with hydrazine hydrate (10.24 g, 0.163 mol) and glacial acetic acid (4.2 mL, 0.074 mol) and the mixture was heated at reflux for 3 hours. The solvent was then evaporated in vacuo. The residue was dissolved in trichloromethane and extracted three times with water to remove the excess of hydrazine hydrate. Evaporation of the organic layer yielded the product (11 g, 0.06 mol, 81%), which was used in the next step without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was then evaporated in vacuo
  4. dissolutionThe residue was dissolved in trichloromethane
  5. extractionextracted three times with water
  6. customto remove the excess of hydrazine hydrate
  7. customEvaporation of the organic layer

Sources & evidence

ORD record
ord-43ac1ad821fb42c2b86eff4526cd5684
Source dataset
uspto-grants-2016_02
Patent number
US09255121B2

Reaction notes

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