Reaction #710591

Reaction equation

ammonium chloride

5,7-dichloro-2-methylamino-8-hydroxyquinoline

potassium carbonate

2-bromopropane

→

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

Yield 78.0%

Solvents

dimethyl sulphoxide

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with dichloromethane (30 mL×3)
2. 2
   Otherdried
3. 3
   Concentrationconcentrated

Procedure

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, 1H), 7.28 (s, 1H), 6.69 (d, J=9.0, 1H), 5.10 (m, 1H), 4.90 (br, 1H), 3.11 (d, J=5.0, 3 H), 1.43 (s, 3H), 1.41 (s, 3H).

Source