Water → 5-Methoxynaphthalen-2-amine

Participants

Reaction Conditions

Reaction Steps

A solution of commercially available 2-amino-5-hydroxynaphthalene (5.16 g, 31.48 mmol) in dimethylformamide (125 ml) was cooled with ice in an inert nitrogen atmosphere. Subsequently, NaH (1.39 g dispersion in a mineral oil at 60%, 34.6 mmoles) was added keeping the temperature below 10° C. and was shaken during 15 min. at ≈5° C. Subsequently methyl iodide (4.47 g, 31.48 mmol) solved in dimethylformamide (5 ml) was added and was left stirring at room temperature during 20 hrs. Water was added and it was evaporated to dryness in a rotavapor. To the remaining residue, water and ethylic ether were added. The aqueous phase was newly extracted with ether and the collection of organic phases was dried over Na2SO4, filtered, and evaporated to dryness. To the resulting crude slurry, a mixture of isopropylic alcohol/petroleum ether 1/1 was added, stirred during a few minutes and the insoluble precipitate was filtered. 4.21 g (77%) of 2-amino-5-methoxynaphthalene were obtained, with a purity determined by HPLC of 99%.

Provenance & Evidence