2-Methoxyaniline → HCID 10559737, compound

Participants

Reaction Steps

2-Anisidine (5.9 ml, 0.05 mole) and 2-dimethylaminoethyl chloride hydrochloride (5.0 g, 0.035 mole) were dissolved in ethanol (75 ml) and treated with sodium carbonate (7.42 g, 0.07 mole). The mixture was heated under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered, and the filtrate evaporated in vacuo. The residue was dissolved in H2O and 10% NaOH solution was added until basic. The mixture was extracted into Et2O, dried (Na2SO4) and evaporated in vacuo to give an orange oil. This was purified by flash column chromatography, eluting with ethyl acetate to afford the title compound as a pale orange oil (3.28 g, 48%).

Provenance & Evidence