Methane → 3-Amino-5-(trifluoromethyl)benzonitrile
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:7]#[N:8])([O-])=O.C.CN(C)N>CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=1)[C:7]#[N:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Nitro-5-trifluoromethylbenzonitrile (1 g, 4.63 mmol) was dissolved in methanol (8 mL) and added activated charcoal (0.1 g), FeCl3.6H2O (17 mg, 0.06 mmol) and N,N-dimethylhydrazine (3.7 mL, 48.6 mmol). The mixture was refluxed overnight. The mixture was filtered and the volatiles removed in vacuo. The residue was purified by chromatography on silica using a mixture of heptane and ethyl acetate (4:1) as eluent affording 3-amino-5-trifluoromethylbenzonitrile.
Workup
- temperatureThe mixture was refluxed overnight
- filtrationThe mixture was filtered
- customthe volatiles removed in vacuo
- customThe residue was purified by chromatography on silica using
- additiona mixture of heptane and ethyl acetate (4:1) as eluent
Sources & evidence
- ORD record
- ord-ac8dc484ef2641ed8a356c7dd29f1fa2
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06503949B1
Reaction notes
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