Methane → 3-Amino-5-(trifluoromethyl)benzonitrile

HRID 1633945Notes

Reaction equation

HRID 1633945 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

HCID 297MethaneHCID 59761,1-DimethylhydrazineHCID 107274333-Cyano-5-nitrobenzotrifluoride

Product 1

HCID 225022643-Amino-5-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThe mixture was filtered
  3. customthe volatiles removed in vacuo
  4. customThe residue was purified by chromatography on silica using
  5. 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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