Acetic Acid → HCID 86657893, compound

HRID 1045345

Reaction equation

HRID 1045345 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 86657893HCID 86657893, compoundYield 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-f717f6b035134c5f95e546611fba502b
Source dataset
uspto-grants-2013_10
Patent number
US08569259B2

Linked notes

Loading…