2-Bromopropane → 5,7-dichloro-2-methylamino-8-isopropoxy-quinoline

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Reaction Steps

A solution of 5,7-dichloro-2-methylamino-8-hydroxyquinoline (1.02 g, 4.21 mmol), anhydrous potassium carbonate (2.4 g) and 2-bromopropane (0.6 mL) in dimethyl sulphoxide (10 mL) was stirred at RT for 2 days. Saturated ammonium chloride solution was added and the mixture was extracted with dichloromethane (30 mL×3). The extracts were combined, dried, and concentrated. The residue, after column chromatography (silica gel, dichloromethane), gave 5,7-dichloro-2-methylamino-8-isopropoxy-quinoline 11 as an off-white solid (938 mg, 78%). 1H NMR (CDCl3): δ 8.13 (d, J=9.0, 1 H), 7.28 (s, 1 H), 6.69 (d, J=9.0, 1 H), 5.10 (m, 1 H), 4.90 (br, 1 H), 3.11 (d, J=5.0, 3 H), 1.43 (s, 3 H), 1.41 (s, 3 H).

Provenance & Evidence