Methyl iodide → 5-methoxynaphthalen-1-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of NaH (7.5 g, 188.0 mmol) in DMF (500 mL) was added a solution of 5-amino-1-naphthol (25.0 g, 157 mmol) dropwise at 0° C. After the addition, mixture was stirred for 30 min at 0° C. and for 1 h at RT. Then a solution of iodomethane (9.82 mL, 157 mmol) in DMF (25 mL) was added dropwise to the mixture at 0° C. and the reaction mixture was allowed to RT and stirred overnight. It was slowly quenched with ice and extracted with EtOAc. The combined organic layers were washed with water, brine, and dried. The solvent was removed under reduced pressure and the residue was purified by column chromatography to afford the title compound (23.0 g, 85%).

Provenance & Evidence