Ammonia → 2-Amino-6-fluoro-4-methoxybenzonitrile

HRID 930454Notes

Reaction equation

HRID 930454 reaction equation
[NH3:1].[F:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7](F)[C:4]=1[C:5]#[N:6]>CS(C)=O>[NH2:1][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:3]([F:2])[C:4]=1[C:5]#[N:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27787722,6-Difluoro-4-methoxybenzonitrile

Product 1

HCID 223351772-Amino-6-fluoro-4-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

Ammonia gas was bubbled through a solution of 2,6-difluoro-4-methoxybenzonitrile (1.0 g, 5.91 mmol) in dimethylsulfoxide (11.83 mL) for 10 minutes. The reaction was then sealed and stirred at 90° C. for 24 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to afford a tan residue. The residue was triturated with water, collected be vacuum filtration, and dried in vacuo to afford the title intermediate (0.9 g, 5.42 mmol) as a white solid. LC/MS (ESI+) m/z=167 (M+H).

Workup

  1. customThe reaction was then sealed
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. concentrationconcentrated in vacuo
  4. customto afford a tan residue
  5. customThe residue was triturated with water
  6. customcollected
  7. filtrationvacuum filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-63e2adcbade6411c98f1d1b012dcd5f5
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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