Ammonia → 2,3-Difluoro-6-nitroaniline

HRID 2227184Notes

Reaction equation

HRID 2227184 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[C:3]=1[F:12].[NH3:13]>>[F:12][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[C:5]([N+:8]([O-:10])=[O:9])[C:4]=1[NH2:13]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 698711,2,3-Trifluoro-4-nitrobenzene

Product 1

HCID 27370282,3-Difluoro-6-nitroanilineYield 84%

Conditions

Temperature
70 °C

Procedure

1,2,3-Trifluoronitrobenzene (20.2 g, 114.1 mmol, Aldrich, Milwaukee) and methanolic ammonia (150 mL of a 2.0 molar solution, Aldrich, Milwaukee) were placed in a sealed tube and were heated to 70° C. for 2 h, after which time the solvents were removed in vacuo. The remaining residue was dissolved in ethyl acetate and was extracted with water, saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and the solvents were removed in vacuo to leave a yellow solid. The title compound was recrystallized from water-methanol to afford yellow needles (16.6 g, 84%); 1H NMR (DMSO-d6) δ: 7.94 (m, 1H, Ar—H), 7.56 (br s, 2H, NH2), 6.72 (m, 1H, Ar—H).

Workup

  1. customafter which time the solvents were removed in vacuo
  2. dissolutionThe remaining residue was dissolved in ethyl acetate
  3. extractionwas extracted with water, saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvents were removed in vacuo
  7. customto leave a yellow solid
  8. customThe title compound was recrystallized from water-methanol

Sources & evidence

ORD record
ord-1bfbdcc732d34954af436b50793dcb7d
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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