Ammonia → 2-Amino-3-fluorobenzonitrile

HRID 1180233Notes

Reaction equation

HRID 1180233 reaction equation
F[C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH3:11]>C(O)C>[CH3:8][CH2:9][CH2:2][CH:3]([CH3:6])[CH3:4].[NH2:11][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 889352,3-Difluorobenzonitrile

Product 2

HCID 78922-MethylpentaneHCID 27833922-Amino-3-fluorobenzonitrileYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2,3-difluorobenzonitrile (19.0 g, 137 mmol) and ethanol (200 ml) pre-saturated with ammonia gas was heated at 140° C. in an autoclave for 8 h (terminal pressure 200 psi). The mixture was allowed to cool to ambient temperature and evaporated to dryness. The residue was dissolved in water (400 ml) and extracted with diethyl ether (2×300 ml). The combined organics were washed with water (300 ml) and brine (250 ml), dried over anhydrous magnesium sulfate, filtered and evaporated. Trituration with isohexane (150 ml) afforded 2-amino-3-fluorobenzonitrile (9.8 g, 50%) as an off-white solid: δH (360 MHz, CDCl3) 4.47 (2H, s), 6.65-6.71 (1H, m), 7.14-7.20 (2H, m).

Workup

  1. temperatureto cool to ambient temperature
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in water (400 ml)
  4. extractionextracted with diethyl ether (2×300 ml)
  5. washThe combined organics were washed with water (300 ml) and brine (250 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-abe1e082cd89443a95e8e84e63861f22
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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