Diethyl Ether → 2-(4-Morpholinyl)ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrochloride
反応式
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:17])[CH:5]=[C:6]([C:13]([O:15][CH3:16])=[O:14])[NH:7]2.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C.OC[CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>>[ClH:1].[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:17])[CH:5]=[C:6]([C:13]([O:15][CH2:16][CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)=[O:14])[NH:7]2参加物
反応条件
- 温度
- 80 °C
実験手順
To a suspension of methyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate (1 g) in 4(2-hydroxyethyl)-morpholine (10 ml) at room temperature was added p-toluene sulphonic acid (20 mg), and the reaction mixture was warmed to 80° C. for 3 hours. The cooled mixture was treated with diethylether (50 ml), the resulting precipitate collected and dissolved in methanol (10 ml) and treated with hydrogen chloride in ethylacetate (2 ml of 5M). The mixture was stirred for 30 minutes and the resulting precipitate collected and recrystallised from ethanol-water to give 2-(4-morpholinyl)ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrochloride (0.45 g), m.p. 233° C. (dec). δ (360 MHz, D2O) 3.35 (4H, bs, morpholinyl-3,5-H), 3.55 (2H, t, CH2N), 4.06 (4H, bs, morpholinyl-2,6-H), 4.85 (2H, t, CO2CH2), 6.73 (1H, s, 3-H), 7.25 (1H, d, 6-H) and 7.40 (1H, d, 8-H). (Found: C, 46.94; H, 4.23; N, 6.84, Cl, 25.92%. C16H16Cl2N2O4. HCl. 0.4H2O requires C, 46.73; H, 4.26; N, 6.81; Cl, 25.86%).
後処理
- customthe resulting precipitate collected
- dissolutiondissolved in methanol (10 ml)
- additiontreated with hydrogen chloride in ethylacetate (2 ml of 5M)
- customthe resulting precipitate collected
- customrecrystallised from ethanol-water
出典と根拠
- ORDレコード
- ord-bd949632648d47308b5ce2d5f3af5cd5
- 出典データセット
- uspto-grants-1993_12
- 特許番号
- US05270309
反応ノート
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