Hydrochloric Acid → 3-Nitro-5-(trifluoromethyl)aniline

HRID 341754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341754
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([F:16])([F:15])[F:14])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-])=O.Cl>CO.O1CCOCC1>[N+:10]([C:8]1[CH:9]=[C:4]([CH:5]=[C:6]([C:13]([F:14])([F:15])[F:16])[CH:7]=1)[NH2:1])([O-:12])=[O:11]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 123060alpha,alpha,alpha-Trifluoro-3,5-dinitrotoluene

Produkt 1

HCID 27757093-Nitro-5-(trifluoromethyl)anilineAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3,5-Dinitrobenzotrifluoride (10 g) was dissolved in a mixture of methanol (200 ml) and 1,4-dioxane (125 ml) and heated under reflux. To this solution was added concentrated hydrochloric acid (30 ml) and then in small portions, reduced iron powder (9 g). CARE: violent effervescence. Refluxing was continued for a further 1 hour and the reaction mixture allowed to cool to room temperature. The mixture was filtered through `Celite` and the pad washed well with dichloromethane. The solvents were removed under reduced pressure to give a residue which was partitioned between dichloromethane and water. The organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure to give a brown semi-solid (8 g). This was chromatographed on silica gel using ethyl acetate-hexane (1:9) as eluant to give the title compound as fine golden crystals, yield 4.98 g.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureRefluxing
  4. filtrationThe mixture was filtered through `Celite` and the pad
  5. washwashed well with dichloromethane
  6. customThe solvents were removed under reduced pressure
  7. customto give a residue which
  8. customwas partitioned between dichloromethane and water
  9. washThe organic layer was washed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9ff402e226dd496eb5af49ee9c998b8a
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856273

Notizen zur Reaktion

Wird geladen…