Ammonium Hydroxide → 5-Amino-2-(trifluoromethyl)benzonitrile

HRID 517723Notes

Reaction equation

HRID 517723 reaction equation
[OH-].[NH4+:2].F[C:4]1[CH:5]=[CH:6][C:7]([C:12]([F:15])([F:14])[F:13])=[C:8]([CH:11]=1)[C:9]#[N:10]>O1CCOCC1>[NH2:2][C:4]1[CH:5]=[CH:6][C:7]([C:12]([F:15])([F:14])[F:13])=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 27375515-Fluoro-2-(trifluoromethyl)benzonitrile

Product 1

HCID 121049585-Amino-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ammonium hydroxide solution (50 mL) was added to a stirred solution of 5-fluoro-2-(trifluoromethyl)benzonitrile (commercially available, for example from Alfa Aesar, Ward Hill, Mass., USA, 2.0 g, 10.6 mmol) in 1,4-dioxane (10 mL) and the reaction mixture was heated to 130° C. for 20 h under 200 psi pressure in a steel bomb. The reaction mixture was evaporated to dryness, and the residue was diluted with DCM and washed with water. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product. This was purified by column chromatography (100-200 mesh silica gel), eluting with 20%-40% EtOAc/petroleum ether, to give the title compound (1.2 g).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionthe residue was diluted with DCM
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product
  7. customThis was purified by column chromatography (100-200 mesh silica gel)
  8. washeluting with 20%-40% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-380356f670df4645a44956b9e8e5707e
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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