Hydrochloric Acid → HCID 10570206, compound

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Reaction Steps

7-Chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (1 g) and 3-dimethylaminopropylamine (30 ml) were heated together in a similar manner to that described for Example 10 to give the crude product, which was suspended in a mixture of 1:1 ethyl acetate and 1N HCl and filtered. The aqueous phase was basified to pH14 with sodium hydroxide and then extracted into ethyl acetate. The organic layer was dried (MgSO4) and the solvent was removed to give the title compound (0.090 g); mp 177°-179° C. (diethyl ether). Found: C, 67.27; H, 6.22; N, 11.61. C20H22ClN3O requires C, 67.50; H, 6.23; N, 11.81%; δ (360 MHz, DMSO-d6) 1.38 (2H, m, NCH2CH2CH2N(CH3)2), 1.98 (2H, m, NCH2CH2CH2N(CH3)2), 2.04 (6H, s, N(CH3)2), 2.58 (2H, m, NCH2CH2CH2N(CH3)2), 6.58 (1H, m, NHCH2CH2CH2N), 7.19-7.94 (8H, m, aromatics), 11.15 (1H, br s, NHCO); m/z (CI-) 355 (M+).

Provenance & Evidence