Water → 1-Naphthylamine

Participants

Reaction Steps

86.6 mg (0.50 mmol) of 1-nitronaphthalene (17), 270 μL (15 mmol) of distilled water and stainless steel balls (50 pieces) were placed in the vessel of the planetary ball mill, which was then closed, and agitated by operating the planetary ball mill for 12 hours at 800 rpm (reversed every 30 minutes). After the lapse of 12 hours, 10 mL of ethyl acetate was added to the vessel of the planetary ball mill to provide a solution containing the reaction mixture, which was then filtered with celite. The operation was repeated 5 times to provide a filtrate, which was then concentrated, thereby providing 44.3 mg (0.31 mmol) of 1-aminonaphthalene (18). The yield was 62%. The conversion yield was 100%, but the isolated yield was lowered since the product was partially distilled off under reduced pressure. The reaction is expressed by the following scheme.

Provenance & Evidence