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4-Ethoxy-m-anisic acid → 1-(4-Ethoxy-3-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 4-Ethoxy-m-anisic acid | HCID 77069 | — |
| 反応物 | 1,2,3,4-Tetrahydro-2-methyl-4-quinolinol | HCID 147634 | — |
| 反応物 | 4-Ethoxy-3-methoxybenzoyl chloride | HCID 12843153 | — |
| 溶媒 | Pyridine | HCID 1049 | — |
| 生成物 | 1-(4-Ethoxy-3-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol | HCID 22339201 | 30% |
反応手順
2-Methyl-1,2,3,4-tetrahydro-4-quinolinol (7.1 g, 43.5 mmol) synthesized in the published manner was dissolved in pyridine (50 ml), followed by addition of 4-ethoxy-3-methoxybenzoyl chloride prepared from 4-ethoxy-3-methoxybenzoic acid (9.2 g, 46.4 mmol). After stirring at room temperature for 16 hours, the reaction mixture was concentrated and extracted by addition of ethyl acetate and water. After the organic layer was dried and concentrated, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/1) and the resulting eluate was recrystallized from ethyl acetate-hexane to give the titled compound (4.4 g, yield: 30%) as a white crystal.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06930104B2 |
| 出典データセット | uspto-grants-2005_08 |
| ORD ID | ord-3cc5cfec28264839b428a7fea88b71be |
| 出典メモ | uspto-grants-2005_08 |