Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 24903131 | HCID 24903131 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 68804532 | HCID 68804532 | 67.8% |
Reaction Steps
A mixture of iron powder (700 mg), acetic acid (60 μl), ethanol (5 ml), and water (3 ml) was stirred with heating at 70° C., and then a mixture of N-ethyl-(3-nitro-5-trifluoromethylpyridin-2-yl)-amine (490 mg) and ethanol (10 ml) was added dropwise. The mixture was stirred with heating at 70° C. for 3 hours. The reaction mixture cooled to room temperature was filtered through Celite®, and the resulting filtrate was concentrated under reduced pressure. The resulting residue was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.29 g of N2-ethyl-5-trifluoromethylpyridin-2,3-diamine (Compound (1F)-8).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08853238B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-524b2903d050450997cfbf6d3cab68b3 |
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| Source note | uspto-grants-2014_10 |
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