Diethyl Ether → 2-(4-Morpholinyl)ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrochloride

HRID 326662노트

반응식

HRID 326662 반응식
[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

참가 물질

5

반응물 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 611632-MorpholinoethanolHCID 14743007Methyl 5,7-dichloro-4-hydroxyquinoline-2-carboxylate

생성물 1

HCID 197351572-(4-Morpholinyl)ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrochloride

반응 조건

온도
80 °C

실험 절차

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%).

후처리

  1. customthe resulting precipitate collected
  2. dissolutiondissolved in methanol (10 ml)
  3. additiontreated with hydrogen chloride in ethylacetate (2 ml of 5M)
  4. customthe resulting precipitate collected
  5. customrecrystallised from ethanol-water

출처 및 근거

ORD 기록
ord-bd949632648d47308b5ce2d5f3af5cd5
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270309

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