Sodium Methoxide → 5-(Methoxymethyl)quinolin-8-ol

Participants

Reaction Steps

5-Chloromethyl-8-hydroxyquinoline hydrochloride (2.145 g; 9.3 mmol) was added to a mixture of sodium methoxide (1.763 g; 32.6 mmol) in MeOH (40 ml). The reaction mixture was stirred for about 4 h at room temperature, and then evaporated to dryness. The residue was dissolved in CHCl3 (100 ml, the solution was washed with water until a neutral pH was obtained, and was then washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was extracted with hexane (100 ml). The hexane solution was evaporated to give the title product, 0.36 g (20%). M.p. 75-760° C. TLC (CHCl3/MeOH/NH3.9.5:0.5:0.1). Rf=0.36.

Provenance & Evidence