Ammonia → 3-Fluoro-2-nitroaniline

HRID 1411392Notes

Reaction equation

HRID 1411392 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].CO>O>[F:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:5]=[CH:6][CH:7]=1)[NH2:12]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 27828343-Fluoro-2-nitroanilineYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a pressure tube was added 1,3-difluoro-2-nitrobenzene (2.8 mL, 26.4 mmol) and 7 N NH3 in CH3OH (10 mL, 70 mmol). The tube was sealed and the mixture was stirred at room temperature for 5 days. The solution was diluted with H2O, extracted with CH2Cl2, and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to give an oil. The oil was triturated with hexane and the resulting orange solid was collected by filtration to give the title compound (2.1 g, 51%).

Workup

  1. customThe tube was sealed
  2. extractionextracted with CH2Cl2
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe oil was triturated with hexane
  9. filtrationthe resulting orange solid was collected by filtration

Sources & evidence

ORD record
ord-2da66ef7de5140059d519a73cf1998ec
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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