反応式
IC(CC)CCC[N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].NC1C=CC=C2C=1N=CC=C2.[ClH:30].CC(O)C>C(O)(C)C>[ClH:30].[C:10]1(=[O:11])[NH:6][C:7](=[O:16])[C:8]2=[CH:15][CH:14]=[CH:13][CH:12]=[C:9]12参加物
実験手順
A solution of 8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)-quinoline (10 g, 29 mmol), prepared as in Example 1, 4-iodo-1-phthalimidohexane (IPH, 10 g, 28 mmol), triethylamine (TEA, 4.5 mL) and 2-ethoxyethanol (10 mL) were heated at 115° for 21/2 hours. One equivalent of IPA and TEA was added and the solution was heated at 115° an additional 2.5 hours. Then one-half equivalent each of IPH and TEA was added and the reaction mixture was heated 5 hours longer. The reaction mixture was diluted with chloroform and washed with water (×3). The organic layer was dried (K2CO3) and concentrated to dryness in vacuo. The oily residue was combined with that obtained from another 8.5 g run and chromatographed over a silica gel column (EM Labs.). Elution with CHCl3 and collection of the fast-moving yellow band afforded the desired phthalimide intermediate (ca. 12 g) contaminated with some IPH. The slower moving material, ca. a 1/1 mixture of product and starting 8-aminoquinoline, was then collected and recycled with IPH and TEA as described above. An additional 7 g of crude product was obtained. The crude material from both runs was combined, dissolved in hot isopropyl alcohol and acidified with 2.7 N HCl-i-PrOH. Pure phthalimide hydrochloride was obtained, 13.2 g (40%), mp 185°-7°.
後処理
- additiona 1/1 mixture of product
- customwas then collected
- customAn additional 7 g of crude product was obtained
出典と根拠
- ORDレコード
- ord-b4dede8496e24bcaad33649a3bb1ab3b
- 出典データセット
- uspto-grants-1984_02
- 特許番号
- US04431807
関連ノート
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