1-Chloromethylnaphthalene → N-Methoxy-1-naphthalenemethanamine

Participants

Reaction Steps

1-Chloromethylnaphthalene (1.85 g, 10 mmol) in 4 ml dimethylformamide (hereinafter DMF) was added dropwise to a mixture of methoxyamine hydrochloride (9.19 g, 110 mmol) and sodium carbonate (11.66 g, 110 mmol) in 100 ml of DMF at 0°-5° C. After stirring 20 minutes, the reaction was warmed to room temperature. After about 18 hours, the reaction was concentrated in vacuo and partitioned between ethyl ether and water. The aqueous layer was extracted twice with ethyl ether. Combined ethereal layers were washed once with water, twice with brine, dried over sodium sulfate and concentrated to 1.19 g of crude product which was further purified by bulb-to-bulb distillation (148°-168° C. at 0.7 mm of Hg), affording 0.947 g of N-methoxy-1-naphthalenemethanamine.

Provenance & Evidence