Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Calcium Chloride | HCID 5284359 | — |
| Reactant | 2-chloro-3-(1-cyanocyclopropyl)-N-{2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide | HCID 57384280 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57387083 | HCID 57387083 | 69% |
Reaction Steps
A suspension of 2-chloro-3-(1-cyanocyclopropyl)-N-{2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (6.60 g, 14.6 mmol), iron powder (1.68 g, 30 mmol) and calcium chloride (3.33 g, 30 mmol) in ethanol (80 mL)-water (20 mL) was stirred at 80° C. overnight. The reaction mixture was poured into 0.5N aqueous sodium hydroxide solution (500 mL), ethyl acetate (300 mL) was added, the mixture was stirred, and the insoluble material was filtered through celite. The ethyl acetate layer was separated from the filtrate, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the title compound (4.23 g, 69%) as a pale-yellow amorphous.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08344135B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-8f8f8ac45b224908b8b415921d128e73 |
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| Source note | uspto-grants-2013_01 |
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