Methyl 5-nitro-2-(trifluoromethoxy)benzoate → Methyl 5-amino-2-(trifluoromethoxy)benzoate
Reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][C:14]([F:17])([F:16])[F:15]>C(O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:13][C:14]([F:15])([F:17])[F:16]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
5-Nitro-2-trifluoromethoxybenzoic acid methyl ester (5.69 g, 21.5 mmol) was dissolved in ethanol 99.9% (80 mL) and stannous (II) chloride dihydrate (24.2 g, 107 mmol) was added. The suspension was stirred on an oil-bath at 75° C. for 2 hours and concentrated in vacuo. Ethyl acetate (100 mL) and water (50 mL) was added and pH was adjusted to pH 8 with 4N sodium hydroxide (50 mL). The liquid was decanted from the precipitation. The precipitate was washed twice with ethyl acetate. The aqueous phase was extracted twice with ethyl acetate (60 mL). The combined organic phases were washed with a saturated sodium chloride solution (2×100 mL), dried (MgSO4) and concentrated in vacuo. Purification by column chromatography (120 g silica) using ethyl acetate and heptane (1:1) as eluent afforded 3.8 g of 5-amino-2-trifluoromethoxybenzoic acid methyl ester.
Workup
- concentrationconcentrated in vacuo
- additionEthyl acetate (100 mL) and water (50 mL) was added
- customThe liquid was decanted from the precipitation
- washThe precipitate was washed twice with ethyl acetate
- extractionThe aqueous phase was extracted twice with ethyl acetate (60 mL)
- washThe combined organic phases were washed with a saturated sodium chloride solution (2×100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customPurification by column chromatography (120 g silica)
Sources & evidence
- ORD record
- ord-50c65e5478a64131a173f981e74bd8e8
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06503949B1
Reaction notes
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