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

HRID 341754Notes

Reaction equation

HRID 341754 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 27757093-Nitro-5-(trifluoromethyl)anilineYield 91.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9ff402e226dd496eb5af49ee9c998b8a
Source dataset
uspto-grants-1999_01
Patent number
US05856273

Reaction notes

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