Ammonia → 2-Amino-6-fluorobenzonitrile

HRID 1061755Notes

Reaction equation

HRID 1061755 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 to air
  6. customdry

Sources & evidence

ORD record
ord-86a939b1858f4610b7c0f615d68ecbd5
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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