5-chloro-2-[2-(dimethylamino)ethoxy]aniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 2-Amino-4-chloro-phenol (1.43 g, 10 mmoles, 1 eq) and potassium carbonate (6.9 g, 50 mmoles, 5 eq) in acetone (25 ml) was added in one portion (2-Chloro-ethyl)-dimethyl-amine hydrochloride (2.16 g, 15 mmoles, 1.5 eq). The reaction mixture was refluxed under Nitrogen for 6 hours at which time the suspension was filtered and the solid washed with acetone. The combined filtrate was concentrated under vacuum and purified by flash chromatography (EtOAc/MeOH/NEt3: 87/9/3) to afford a beige solid (1.6 g, yield=72%). The reaction mixture was refluxed under Nitrogen for 6 hours at which time the suspension was filtered the solid washed with acetone The combined filtrate was concentrated under vacuum purified by flash chromatography (EtOAc/MeOH/NEt3: 87/9/3)