Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | Benzyloxyamine hydrochloride | HCID 102312 | — |
| Reactant | 2-Amino-4,5-difluorobenzoic acid | HCID 735965 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 15908874 | HCID 15908874 | 69.6% |
Reaction Steps
Carbonyldiimidazole (6.1 g, 37 mmol) was added to a suspension of 4,5-difluoroanthranilic acid (5.40 g, 31 mmol) in 250 mL of THF, and the mixture was stirred for 24 hours at 25° C. O-benzylhydroxylamine hydrochloride (4.95 g, 31 mmol) and triethylamine (5.2 mL, 37 mmol) were added, and the mixture was heated to reflux for 4 hours. The reaction mixture was concentrated and washed with 1N HCl, saturated NaHCO3, brine, and dried over magnesium sulfate. The solution was concentrated to give 6.0 g of the title compound as a solid, mp 125-126° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06825199B2 |
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| Source dataset | uspto-grants-2004_11 |
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| ORD ID | ord-26521e26d639403c91e995ed6687e50d |
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| Source note | uspto-grants-2004_11 |
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