Hydrochloric Acid → 4-Methoxy-3-(trifluoromethoxy)aniline

HRID 638924Notes

Reaction equation

HRID 638924 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][C:13]([F:16])([F:15])[F:14])[CH:5]=1)([O-])=O.Cl>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][C:13]([F:14])([F:15])[F:16])[CH:5]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 686863511-Methoxy-4-nitro-2-(trifluoromethoxy)benzene

Product 1

HCID 571118334-Methoxy-3-(trifluoromethoxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 4-nitro-2-trifluoromethoxyanisole (500 mg, 2.11 mmol) in MeOH (8.0 mL) at room temperature was added aqueous HCl solution (1.0 mL, 3.0 M) followed by 10% Pd/C (80 mg). The reaction mixture was stirred under H2 atmosphere for 17 h, filtered through a pad of celite and concentrated to give 4-amino-2-trifluoromethoxyanisole as a hydrochloride salt (500 mg). The product was used without further purification.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2f4270a8cb01410c8810f851f3004318
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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