Acetic Acid → N'-methyl-5-trifluoromethyl-benzene-1,2,3-triamine
Reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([N+:14]([O-])=O)[C:5]=1[NH:17][CH3:18])([O-])=O.C(O)(=O)C>[Fe].C(O)C>[CH3:18][NH:17][C:5]1[C:4]([NH2:1])=[CH:9][C:8]([C:10]([F:11])([F:13])[F:12])=[CH:7][C:6]=1[NH2:14]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of (2,6-dinitro-4-trifluoromethyl-phenyl)-methyl-amine (5.0 g), acetic acid (11 mL), ethanol (100 ml), and ice (20 g), iron powder (6.4 g) was added under ice-cooling. The reaction mixture was stirred at 0° C. for 3.5 hours, and filtered through Celite®. The resulting filtrate was concentrated under reduced pressure, and diluted with 1N aqueous sodium hydroxide solution. The solution was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 3.1 g of N′-methyl-5-trifluoromethyl-benzene-1,2,3-triamine. N′-methyl-5-trifluoromethyl-benzene-1,2,3-triamine
Workup
- additionwas added under ice-
- temperaturecooling
- filtrationfiltered through Celite®
- concentrationThe resulting filtrate was concentrated under reduced pressure
- additiondiluted with 1N aqueous sodium hydroxide solution
- extractionThe solution was extracted with ethyl acetate
- dry with materialThe combined organic layer was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3a74a697bb8e448891be94d92f63e724
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278983B2
Reaction notes
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