2-(Dimethylamino)ethanol → 5-(2-Dimethylamino-ethoxy)-2-nitro-phenylamine

Participants

Reaction Conditions

Reaction Steps

3-Fluoro-6-nitroaniline (0.7 g, 4.48 mmol) and N,N-dimethylethanolamine (1.34 mL, 13.45 mmol) were dissolved in toluene (5 mL). This solution was cooled at 0° C. and finely ground KOH (1.258 g, 22.4 mmol) was added to the stirring mixture. The reaction mixture was stirred for 16 hours at room temperature, diluted with H2O (30 mL) and then extracted with CHCl3 (3×25 mL). The combined organics were dried (Na2SO4), filtered and the solvent was removed in vacuo. Purification by SiO2 chromatography (0% to 10% 2.0M NH3 in MeOH/dichloromethane) gave 5-(2-dimethylamino-ethoxy)-2-nitro-phenylamine as a dark oil (0.665 g, 90%). MS(ESI) m/z 226.0 (M+H)+

Provenance & Evidence