Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Reactant | HCID 178484335 | HCID 178484335 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 135967941 | HCID 135967941 | — |
Reaction Steps
To a solution of hydroxylamine hydrochloride (354 mg, 5.1 mmol) in an a mixture of aqueous 5N sodium hydroxide solution (1 mL, 5 mmol), acetic acid (10 mL) and dioxane (8.5 mL) was added the N-[(1E)-(dimethylamino)methylene]-4-hydroxybenzamide from step 1 of this Example (815 mg, 4.24 mmol). The reaction was stirred at 90° C. for 3 hrs. Upon cooling to room temperature, the solvent was removed under vacuum and residue was purified by column chromatography on an 80 gram biotage silica gel cartridge eluting with 20-50% ethyl acetate/hexanes (gradient) to give the product as white solid. LRMS calc: 162.0; obs: 163.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08343990B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-a1627fe981cc4c7b8f8c4df3dc75b45a |
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| Source note | uspto-grants-2013_01 |
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