Acetic Acid → 3-Amino-5-(trifluoromethyl)benzonitrile

HRID 1887559Notes

Reaction equation

HRID 1887559 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(O)(=O)C.[Sn](Cl)Cl>CCO.O>[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

6

Reactant 3

HCID 176Acetic AcidHCID 24479Stannous ChlorideHCID 107274333-Cyano-5-nitrobenzotrifluoride

Product 1

HCID 225022643-Amino-5-(trifluoromethyl)benzonitrileYield 49.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-nitro-5-(trifluoromethyl)benzonitrile (500 mg, 2.31 mmol) and acetic acid (6.62 mL, 116 mmol) in EtOH (10 mL) and water (10 mL) is added tin (II) chloride (2.61 g, 11.6 mmol) and the reaction mixture is heated at 80° C. for 6 h. The solvent is removed in vacuo and then the residue is portioned between DCM and 4 N HCl solution. The organic layer separated and then dried over anhydrous Na2SO4, filtered and concentrated. The residue is then separated via FCC (10-100% EtOAc/heptane) to give the compound as a yellow oil (213 mg, 49%). MS (ESI) m/z 185.3 (M+1).

Workup

  1. customThe solvent is removed in vacuo
  2. customThe organic layer separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is then separated via FCC (10-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-51b550fcbb1e42cba490f8efdaf54511
Source dataset
uspto-grants-2013_08
Patent number
US08501756B2

Reaction notes

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