Ammonia → 2,3,5-Trifluoro-6-nitroaniline

HRID 412726

Reaction equation

HRID 412726 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[N+:11]([O-:13])=[O:12].[NH3:14].O1CCOCC1>O>[F:8][C:7]1[C:6]([F:9])=[CH:5][C:4]([F:10])=[C:3]([N+:11]([O-:13])=[O:12])[C:2]=1[NH2:14]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 675661,2,3,5-Tetrafluoro-4-nitrobenzene

Product 1

HCID 2230852,3,5-Trifluoro-6-nitroanilineYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution comprising 2,3,4,6-tetrafluoronitrobenzene (0.6 g, 3.1 mmol) and ammonia in dioxane (Aldrich, 0.5M, 7.5 mmol) was stirred at room temperature for 3 hours to give a fine white precipitate. The mixture was diluted with an equal volume of water to dissolve the white precipitate and give yellow crystals. The crystals were isolated were collected and dried to provide 2,3,5-trifluoro-6-nitroaniline (307 mg, 51%) as yellow needles; m.p. 66° C.; 1H NMR (CDCl3) δ 6.4 (1H, m), δ 6.0 (2H, s).

Workup

  1. customto give a fine white precipitate
  2. dissolutionto dissolve the white precipitate
  3. customgive yellow crystals
  4. customThe crystals were isolated
  5. customwere collected
  6. customdried

Sources & evidence

ORD record
ord-63bd390fc9ae4e0e94c0a4d53118d5a4
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Linked notes

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