Ammonia → 2-Amino-6-fluoro-4-methoxybenzonitrile
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction was then sealed
- temperatureThe reaction mixture was cooled to ambient temperature
- concentrationconcentrated in vacuo
- customto afford a tan residue
- customThe residue was triturated with water
- customcollected
- filtrationvacuum filtration
- customdried in vacuo
Sources & evidence
- ORD record
- ord-63e2adcbade6411c98f1d1b012dcd5f5
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296734B2
Reaction notes
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