Diethylamine → N,N-Diethyl-3-fluoro-4-nitrobenzamide

Participants

Reaction Steps

3-Fluoro-4-nitrobenzoic acid (5.0 g, 27.0 mmol) was refluxed in a mixture of 2:1 CH2Cl2/SOCl2 (150 mL) overnight. The solvent was concentrated and the residue dissolved in CH2Cl2 (50 mL). Another CH2Cl2 solution (50 mL) of diethylamine (3.35 mL, 1.2 eq) and triethylamine (7.5 mL, 2 eq) was then added dropwise to the cold stirring solution (0° C.) of the acid chloride. The solution was stirred at rt for 1 h. The solution was then washed with 5% KHSO4 solution, saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by flash chromatography using 2:1/hex:EtOAc on silica gel to afford the title compound (5.10 g, 79% yield); 1H NMR (400 MHz, CDCl3) δ 8.12 (m, 1H), 7.29 (m, 2H), 3.56 (br d, 2H), 3.23 (br d, 2H), 1.27 (br s, 3H), 1.15 (br s, 3H).

Provenance & Evidence