Methyl 4-nitro-2-(trifluoromethyl)benzoate → Methyl 4-amino-2-(trifluoromethyl)benzoate

HRID 1994124Notes

Reaction equation

HRID 1994124 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1)([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>CCOC(C)=O>[NH2:1][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:14]([F:15])([F:16])[F:17])[CH:5]=1

Participants

4

Reactant 2

HCID 46311176Methyl 4-nitro-2-(trifluoromethyl)benzoateHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 46311081Methyl 4-amino-2-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-nitro-2-(trifluoromethyl)benzoate (5.20 g, 20.9 mmol) was dissolved in EtOAc (100 mL) and tin chloride dihydrate (9.41 g, 41.7 mmol) was added to the reaction mixture. The reaction was heated at reflux for 2 h. The crude reaction mixture was purified by column chromatography (SiO2, EtOAc/hexanes) to give the title compound. LCMS: (FA) ES− 218.4 (M−1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 h
  3. customThe crude reaction mixture
  4. customwas purified by column chromatography (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-5142fc929ec341fcbdd87482b31c9991
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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