Diethylethanolamine → Ethyl 2-(2-diethylaminoethoxy)-5-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

1.06 g (5.00 mmol) of ethyl 2-fluoro-5-nitrobenzoate and 0.58 mL (5.00 mmol) of 2-diethylaminoethanol are dissolved in 20 mL of DMF and at 0° C. 0.36 g (7.45 mmol) of sodium hydride (50%) is added. The mixture is stirred for 45 minutes at 0° C., poured onto ice water, and finally extracted three times with ethyl acetate. The organic phase is dried over sodium sulfate, the solvent is eliminated and the residue is purified through a silica gel column with petroleum ether/ethyl acetate (4:1) as eluant. Yield: 0.30 g (19% of theory); C15H22N2O5 (M=310.35); calc.: molecular ion peak (M+H)+: 311; found: molecular ion peak (M+H)+: 311; Rf value: 0.1 (silica gel, petroleum ether/ethyl acetate (4:1)).

Provenance & Evidence