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Trifluoroacetic acid → N-(2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Trifluoroacetic acid | HCID 6422 | — |
| 反応物 | Oxyselenide | HCID 167175 | — |
| 反応物 | 1-Isopropyl-3-methoxy-benzene | HCID 10931606 | — |
| 反応物 | N-(2,2-dihydroxy-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide | HCID 86717356 | — |
| 溶媒 | Acetic Acid | HCID 176 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | N-(2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide | HCID 71476974 | 20% |
反応手順
N-(2,2-dihydroxy-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide (1.50 g, 6.4 mmol) was completely dissolved in anhydrous dioxane (15 ml). This solution was added with selenium oxide (1.56 g, 14.0 mmol) and AcOH (1.5 ml). The reaction mixture was heated for 12 hrs under reflux. After filtration at high temperature, the filtrate was concentrated to afford 1.79 g (100%). A trifluoroacetic acid solution of the resulting product was added with isopropyl-3-methoxy benzene (962 mg, 6.4 mmol) followed by stirring for 12 hours. The resulting product was extracted with ethyl acetate, and concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:1) to afford the title compound (0.52 g, 20%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09346749B2 |
| 出典データセット | uspto-grants-2016_05 |
| ORD ID | ord-636090814dc841c0bdc11ee7db9a4840 |
| 出典メモ | uspto-grants-2016_05 |