Diethyl Ether → 2-(4-Morpholinyl)ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrochloride
Reaction equation
[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]2Participants
Conditions
- Temperature
- 80 °C
Procedure
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%).
Workup
- 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
Sources & evidence
- ORD record
- ord-bd949632648d47308b5ce2d5f3af5cd5
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05270309
Reaction notes
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