Hydrochloric Acid → 2-Nitro-6-(trifluoromethoxy)aniline

HRID 2242043Notes

Reaction equation

HRID 2242043 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.[I-].C[N+:17](C)(C)N.CC([O-])(C)C.[K+].Cl>CS(C)=O>[N+:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:13])([F:14])[F:1])[C:5]=1[NH2:17])([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 18683Hydrazinium, 1,1,1-trimethyl-, iodide (1:1)HCID 27772971-Nitro-3-(trifluoromethoxy)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 669159442-Nitro-6-(trifluoromethoxy)aniline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-trifluoromethoxy nitrobenzene (4.0 g, 20 mmol) in DMSO (60 ml), trimethylhydrazinium iodide (4.4 g, 22 mmol) is added and cooled to 0° C. KOt-Bu is added in portions. After stirring for 4 h at 25° C., ice water is added, pH is adjusted to 2-3 with HCl solution, the mixture extracted with EtOAc and washed with brine, followed by drying (Na2SO4) and evaporation of the solvent. Chromatography (silica gel, CH2Cl2/hexane=1:1) gave 2-nitro-6-trifluoromethoxy-phenylamine.

Workup

  1. extractionthe mixture extracted with EtOAc
  2. washwashed with brine
  3. customby drying
  4. custom(Na2SO4) and evaporation of the solvent

Sources & evidence

ORD record
ord-bd5239cbbae9487da39605c7ff37aac0
Source dataset
uspto-grants-2010_03
Patent number
US07671063B2

Reaction notes

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