Hydrochloric Acid → 2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-5-chloro-1H-quinolin-4-one dihydrochloride

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Reaction Steps

2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-5-chloro-4-methoxyquinoline (78 mg, 0.18 mmol) in dioxane:concentrated aq. HCl 1:2 (7 ml) was heated at 80° C. for 18 h. Volatiles were evaporated in vacuo and the residue was triturated with CHCl3:tBuOMe 2:1 and filtered to give the title compound as a colourless solid, (30 mg, 34%). δH (CD3OD) 2.10-2.27 (m, 2H, CH2CH2CH2), ca. 3.27 (t, merged with MeOH peak, 2H, CH2CH2CH2), 3.67 (t, J=6.7, 2H, CH2CH2CH2), 4.29 (s, 2H, Ar—CH2—N), 6.39 (s, 1H, HCC═O), 7.47-7.56 (m, 2H, Ar—H), 7.60-7.72 (m, 2H, Ar—H), 7.78-7.90 (m, 2H, Ar—H); MS (ES+) 410 (MH+, 59%), 235 (100).

Provenance & Evidence