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

HRID 453132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453132
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 225022643-Amino-5-(trifluoromethyl)benzonitrileAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-214ee871d1e341649dd656e4c29b228c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492393B2

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