Ethanol → HCID 69978275, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (6-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-acetic acid ethyl ester (2.0 g, 8.0 mmol) in N,N-dimethylformamide (16 mL) was treated with a solution of sodium ethoxide (21 wt %) in ethanol (3.0 mL, 8.0 mmol) at rt and after 15 min, (3-bromopropyl)-carbamic acid tert-butyl ester (1.9 g, 8.0 mmol) was added. After 4 days, the solution was treated with water (75 mL) and the resulting gum was briefly heated, then cooled to 0° C. The precipitated solid was triturated for 6 h, to give the crude product (2.7 g). Flash chromatography (90 g silica; CHCl3, then 1% MeOH (saturated with NH3) —CHCl3) gave the title compound (2.6 g, 79% yield) as a white solid.

Provenance & Evidence