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

HRID 326663Notes

Reaction equation

HRID 326663 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-bacfef79b4e04e7d96ad894a70a4a02b
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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