Potassium Nitrate → 4,5-Difluoro-2-nitroaniline

HRID 2107586Notes

Reaction equation

HRID 2107586 reaction equation
CC([NH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([F:12])[CH:6]=1)=O.[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[N+:13]([C:10]1[CH:9]=[C:8]([F:11])[C:7]([F:12])=[CH:6][C:5]=1[NH2:4])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 223109N-(3,4-Difluorophenyl)acetamide

Product 1

HCID 1571514,5-Difluoro-2-nitroanilineYield 62.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3,4-difluoroacetanilide (85.5 g) in sulfuric acid (850 ml) is added gradually with stirring potassium nitrate (55.5 g) at room temperature during which the temperature raises to 60° C. The mixture is stirred at 60° C. for one hour. The reaction mixture is poured into ice water, and the precipitated crystals are taken by filtration. The precipitates are dissolved in dichloromethane and washed with aqueous sodium hydrogen carbonate, water and aqueous saturated sodium chloride in this order and dried. The solvent is removed by concentration and washed with n-hexane. The resulting crystals are taken by filtration and dried to give 2-nitro-4,5-difluoroaniline (54 g).

Workup

  1. filtrationthe precipitated crystals are taken by filtration
  2. dissolutionThe precipitates are dissolved in dichloromethane
  3. washwashed with aqueous sodium hydrogen carbonate, water and aqueous saturated sodium chloride in this order
  4. customdried
  5. customThe solvent is removed by concentration
  6. washwashed with n-hexane
  7. filtrationThe resulting crystals are taken by filtration
  8. customdried

Sources & evidence

ORD record
ord-00bef8aaa4a04208a75d33143d4e679e
Source dataset
uspto-grants-1990_06
Patent number
US04935420

Reaction notes

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