Sodium hydride → HCID 15053135, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.50 g) and 2-chloromethylquinoline hydrochloride (0.60 g) were suspended in 6 mL of dimethylformamide and 60% sodium hydride (0.224 g) was added. When gas evolution ceased, the bath temperature was raised to 50° C. for 2 hours. The reaction mixture was quenched with 0.1 mL of acetic acid and was diluted with ethyl acetate (75 mL). The mixture was washed with water (2×25 mL) and brine (1×25 mL), dried (MgSO4) and chromatographed over 100 g of silica gel, eluting with dichoromethane-ethyl acetate (50: 1) to give 0.39 g of 4-[(2-quinolinyl)methoxy]-alpha-oxobenzeneacetic acid methyl ester, mp 109°-110° C.

Provenance & Evidence