Ammonia → 3-Fluoro-2-nitroaniline

HRID 475224Notes

Reaction equation

HRID 475224 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[N+:9]([O-:11])=[O:10].[NH3:12]>CCO>[F:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 27828343-Fluoro-2-nitroanilineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1,3-difluoro-2-nitro-benzene (30 g, 0.188 moles) in EtOH (300 mL) was added 25% aq. ammonia solution (300 mL) and the resulting mixture was heated to 75° C. for 16 h then cooled and concentrated in vacuo. The residue was dissolved in EtOAc, washed with water and brine solution, dried (Na2SO4), filtered and concentrated to afford 25 g (85%) of 3-fluoro-2-nitro-phenylamine (138) as a brown solid which was used without any further purification.

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water and brine solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c5cc3d9576ed4eea843772b00f798f04
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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