Ammonia → 2-Amino-6-fluorobenzonitrile

HRID 1180236Notes

Reaction equation

HRID 1180236 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:3]=1[C:4]#[N:5].[NH3:11]>C(O)C>[NH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 5226592-Amino-6-fluorobenzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2,6-difluorobenzonitrile (19.0 g, 137 mmol) and ethanol (200 ml) pre-saturated with ammonia gas was heated at 140° C. in an autoclave for 6 h (terminal pressure 200 psi). The mixture was allowed to cool to ambient temperature, evaporated to dryness and triturated with water (200 ml). The solid was filtered and left to air-dry to afford 2-amino-6-fluorobenzonitrile (18.0 g, 97%) as an off-white solid: δH (360 MHz, CDCl3) 4.53 (3H, s), 6.44-6.52 (2H, m), 7.24-7.30 (1H, m).

Workup

  1. temperatureto cool to ambient temperature
  2. customevaporated to dryness
  3. customtriturated with water (200 ml)
  4. filtrationThe solid was filtered
  5. waitleft
  6. customto air-dry

Sources & evidence

ORD record
ord-db57eef7a9d8439abc5dd6e32417620e
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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