Ethanol → Methyl 3-amino-2-methyl-5-(trifluoromethyl)benzoate
Reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([C:15]([F:18])([F:17])[F:16])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(O)C.[NH4+].[Cl-]>[Fe]>[NH2:12][C:11]1[C:2]([CH3:1])=[C:3]([CH:8]=[C:9]([C:15]([F:16])([F:17])[F:18])[CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a stirred solution of methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate (1 equiv.) in ethanol (2 mL per 1 mmol), was added NH4Cl solution (5.1 equiv., dissolved in water. Volume of water equivalent to volume of ethanol) followed by Fe powder (8 equiv.). the resulting reaction mixture was stirred at 90° C. for 1 h. On completion, the reaction mixture was filtered and the filtrate concentrated till dryness. The resulting solid was dissolved in saturated sodium bicarbonate solution and the aqueous layer extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford solid methyl 3-amino-2-methyl-5-(trifluoromethyl)benzoate in quantitative yield.
Workup
- customthe resulting reaction mixture
- filtrationOn completion, the reaction mixture was filtered
- concentrationthe filtrate concentrated till dryness
- dissolutionThe resulting solid was dissolved in saturated sodium bicarbonate solution
- extractionthe aqueous layer extracted with ethyl acetate
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b88b15f9ff21444ea32a677f98bdd332
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598167B1
Reaction notes
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