Benzyl Bromide → (8-(Benzyloxy)quinolin-5-yl)methanol

Participants

Reaction Steps

5-(Hydroxymethyl)-8-hydroxyquinoline (1) (6.44 g, 36.75 mmol) was dissolved in dry dimethylformamide (40 ml) and sodium hydride (1.3 g of 80% suspension in mineral oil, corresponding to 1.04 g, 43.3 mmol) was added. The mixture was stirred until hydrogen evolution ceased (~45 min). Benzyl bromide (4.5 ml, 6.47 g, 37.8 mmol) was added and the mixture was stirred for 4 h. The solution was poured into water (350 ml) and stirred for 20 min, and the precipitate was filtered and washed with water. After crystallization from benzene, 5.4 g of product (2) was obtained; mp 192°-194° C. An analytical sample was recrystallized from toluene; Rf 0.68 (chloroform-methanol, 9:1).

Provenance & Evidence