4-Fluoro-3-nitrobenzonitrile → 3-Amino-4-fluorobenzonitrile
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-])=O>CC(O)=O.[Fe]>[NH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[F:1])[C:6]#[N:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 4-fluoro-3-nitrobenzonitrile (5.0 g, 30.1 mmol) and Fe powder (5.05 g, 90.3 mmol) in AcOH (100 mL) was heated at 80° C. for 1 hour under N2. Then the solvent was removed under vacuum and water (200 mL) was added to the residue. The solution was adjusted to pH 6 by addition of Na2CO3 and extracted with DCM (2×200 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated to yield 3-amino-4-fluorobenzonitrile (48), which was used without further purification. MS m/z 137.0 (M+1)+.
Workup
- customThen the solvent was removed under vacuum and water (200 mL)
- additionwas added to the residue
- additionThe solution was adjusted to pH 6 by addition of Na2CO3
- extractionextracted with DCM (2×200 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-620224e272d7452d9489c878cde389ff
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754071B2
Reaction notes
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