Ammonia → 2-Amino-3,5-difluorobenzonitrile

HRID 586284Notes

Reaction equation

HRID 586284 reaction equation
F[C:2]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH3:12]>C(O)C>[NH2:12][C:2]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27769982,3,5-Trifluorobenzonitrile

Product 1

HCID 146519902-Amino-3,5-difluorobenzonitrileYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,3,5-trifluorobenzonitrile (25.0 g, 159 mmol) and ethanol (300 ml) pre-saturated with ammonia gas was heated at 120° C. in an autoclave for 8 h. The mixture was allowed to cool to ambient temperature and evaporated to dryness. The residue was partitioned between water (1 l) and ethyl acetate (1 l). The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified by flash chromatography (silica gel, CH2Cl2) to afford 3.7 g (15%) of the title compound as a cream solid: 1H NMR (360 MHz, CDCl3) δ 4.08 (2H, s), 6.60-6.64 (1H, m), 6.67-6.72 (1H, m).

Workup

  1. temperatureto cool to ambient temperature
  2. customevaporated to dryness
  3. customThe residue was partitioned between water (1 l) and ethyl acetate (1 l)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-ed00e30c01ac48dbbff80bc1a197670f
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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