Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | 4-(Trifluoromethyl)anthranilic acid | HCID 67869 | — |
| Reactant | Cyclopropanecarbonyl chloride | HCID 77637 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68753912 | HCID 68753912 | — |
Reaction Steps
Cyclopropanecarbonyl chloride (2.71 ml, 29.6 mmol) was added to a solution of 2-amino-4-(trifluoromethyl)benzoic acid (2.00 g, 9.75 mmol) in THF (50 mL) followed by pyridine (4.07 ml, 50.3 mmol). The mixture was stirred at 70° C. overnight. The mixture was cooled at 0° C., hydrazine was added, and the reaction was stirred at room temperature for 30 minutes and then at 75° C. for 24 hours. The reaction was cooled at 22° C., diluted with ethyl acetate, washed with aq. NaHCO3, dried with magnesium sulfate, filtered, and concentrated. The residue was suspended in toluene and concentrated again. The process was repeated to obtain the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08962639B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-e03a4f8e53e7447d8f4f6d84a8ba3c32 |
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| Source note | uspto-grants-2015_02 |
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