Sodium hydride → HCID 21107320, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (60%, 0.27 g, 6.6 mmol) in anhydrous N,N-dimethylformamide (30 ml) was added a pre-cooled solution of acetic acid 1-bromomethyl-2-(6-hydroxyquinolin-5-yl)ethyl ester (intermediate 8) (1.96 g, 6.0 mmol) in 10 ml of N,N-dimethylformamide at 0° C. The reaction mixture was stirred at 0° C. for 1 hr, quenched with water, and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum. Chromatography (10% hexanes-ethyl acetate) afforded 0.89 g (61%) of 2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-yl acetate as a white solid: mp 125.4–127° C. MS ESI m/z 244 [M+H]+. Elemental Analysis for C14H13NO3: Calculated: C, 69.12; H, 5.39; N, 5.76. Found: C, 69.12; H, 5.48; N, 5.64.

Provenance & Evidence