Hydrochloric Acid → 5,7-Dichloro-2-[2-(4-morpholinyl)ethyl]carbamoyl-4-oxo-1,4-dihydroquinoline hydrochloride

HRID 326663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 326663
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[Cl:10][C:11]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]2[C:12]=1[C:13](=[O:26])[CH:14]=[C:15]([C:22](OC)=[O:23])[NH:16]2.C(N(CC)CC)C.Cl>O.C(OCC)(=O)C.CO>[ClH:10].[Cl:10][C:11]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]2[C:12]=1[C:13](=[O:26])[CH:14]=[C:15]([C:22](=[O:23])[NH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)[NH:16]2

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 14743007Methyl 5,7-dichloro-4-hydroxyquinoline-2-carboxylate

Produkt 1

HCID 197352005,7-Dichloro-2-[2-(4-morpholinyl)ethyl]carbamoyl-4-oxo-1,4-dihydroquinoline hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 4-(2-aminoethyl)morpholine (10 ml) was added methyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate (1 g) followed by triethylamine (1 ml) and the solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate (5×50 ml), the combined organic layers were washed with water (2×50 ml), brine (2×50 ml) and dried over magnesium sulphate. The solvent was removed under reduced pressure to yield a crude product (0.4 g). The aqueous layer yielded a further 0.9 g of crude product after standing overnight. The combined crude product was treated with methanol (5 ml) and hydrogen chloride in ethyl acetate (5 ml of 5M), to give a white crystalline product which was recrystallised from ethanol-water to yield 5,7-dichloro-2-[2-(4-morpholinyl)ethyl]carbamoyl-4-oxo-1,4-dihydroquinoline hydrochloride (0.63 g), m.p.>280° C. δ (360 MHz, D2O) 3.48 (6H, CH2N and morpholinyl-3,5-H), 3.86 (2H, t, CONHCH2), 4.00 (4H, bs, morpholinyl-2.6-H), 6.63 (1H, s, 3-H), 7.33 (1H, d, 6-H) and 7.54 (1H, d, 8-H), (Found: C, 46.36: H, 4.57: N, 10.12; Cl, 24.80%. C16H17Cl2N3O3.HCl.H2O requires C, 46.23; H, 4.61, N, 10.11; Cl, 25.59%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (5×50 ml)
  2. washthe combined organic layers were washed with water (2×50 ml), brine (2×50 ml)
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was removed under reduced pressure
  5. customto yield a crude product (0.4 g)
  6. customThe aqueous layer yielded a further 0.9 g of crude product
  7. waitafter standing overnight
  8. customto give a white crystalline product which
  9. customwas recrystallised from ethanol-water

Quellen und Nachweise

ORD-Eintrag
ord-bacfef79b4e04e7d96ad894a70a4a02b
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270309

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