Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].O.C(O)(=O)C>C(OCC)(=O)C.[Fe]>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]Participants
Conditions
- Temperature
- 50 °C
Procedure
57 g (0.23 mol) of N-(3-fluoro-4-methylphenyl)-3-nitro-2-pyridylamine was dissolved in ethyl acetate (250 ml), and water (125 ml) and acetic acid (80 ml) were added thereto, and the solution was heated to 50° C. 77 g (1.40 mol) of iron powder was added to the reaction solution so that the temperature thereof would not exceed 60° C., and then stirred for 1 hour at 60° C. The reaction solution was cooled to room temperature, and the inorganic matter was separated by filtration. The solution was extracted with ethyl acetate, and washed with saturated brine, and then the obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue thus obtained was washed with hexane to obtain 45 g (yield: 90%) of N2-(3-fluoro-4-methylphenyl)-2,3-pyridinediamine.
Workup
- customexceed 60° C.
- temperatureThe reaction solution was cooled to room temperature
- customthe inorganic matter was separated by filtration
- extractionThe solution was extracted with ethyl acetate
- washwashed with saturated brine
- dry with materialthe obtained organic layer was dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe residue thus obtained
- washwas washed with hexane
Sources & evidence
- ORD record
- ord-39e70946f51543468e3c9d6cc7fbb0e3
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389523B2
Linked notes
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