Hydrochloric Acid → 2-Methoxy-5-(trifluoromethyl)aniline

HRID 2166793Notes

Reaction equation

HRID 2166793 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[N+:13]([O-])=O.Cl>C(O)(C)C.O.[Fe]>[NH2:13][C:4]1[CH:5]=[C:6]([C:9]([F:10])([F:11])[F:12])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 967482-Nitro-4-trifluoromethylanisole

Product 1

HCID 6006372-Methoxy-5-(trifluoromethyl)anilineYield 82.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

4-Methoxy-3-nitrobenzotrifluoride (95 g) in isopropanol (1.0 liter) and water (250 ml) was mixed with concentrated hydrochloric acid (15 ml). Iron powder (180 g) was added and the mixture was heated and stirred under reflux. After 90 minutes the mixture was cooled to 50° C. and filtered. The residue was washed with isopropanol and the combined filtrates evaporated. The residue was dissolved in toluene and the solution dried (MgSO4) and evaporated. The residue was triturated with light petroleum (b.p. 30°-40°) to give the 3-amino-4-methoxybenzotrifluoride as a colourless solid (68 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. filtrationfiltered
  4. washThe residue was washed with isopropanol
  5. customthe combined filtrates evaporated
  6. dissolutionThe residue was dissolved in toluene
  7. dry with materialthe solution dried (MgSO4)
  8. customevaporated
  9. customThe residue was triturated with light petroleum (b.p. 30°-40°)

Sources & evidence

ORD record
ord-102710fbc4b74a5e9e11278dd0018ecb
Source dataset
uspto-grants-1983_06
Patent number
US04388472

Reaction notes

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