Sodium hydride → HCID 54227746, compound

Participants

Reaction Steps

A solution of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.376 g) in dimethylformamide (5 mL) was treated with 55% sodium hydride (0.085 g), stirred for 15 minutes and then 5-(3-bromopropyl)-5,6-dihydro-6-oxophenanthridine (0.613 g) in dimethylformamide (5 mL) was added. The mixture was stirred at room temperature for 22 hours and worked up as in Example 20. The residual oil was purified by HPLC (ethyl acetate-hexane; 7:13), and crystallization of the resulting solid from ethyl acetate-tetrahydrofuran gave 0.4 g of 4-[3-(5,6-dihydro-6-oxo-5-phenanthridinyl)propoxy]-alpha-oxobenzeneacetic acid ethyl ester, mp 95°-97° C. A second crop of the title compound (0.16 g, mp 95°-97° C.) was recovered from the mother liquor.

Provenance & Evidence