7-Bromo-1-nitronaphthalene → 7-Bromonaphthalen-1-amine

Participants

Reaction Steps

To a suspension of iron powder (1.66 g) in 25 ml water and 25% HCL (1.7 ml) was added 2-bromo-8-nitro-naphthalene (2.15 g, 8.5 mmol) and the reaction mixture was refluxed for 2 hours. The aqueous phase was extracted with ethyl acetate to give the crude product. Chromatography on silica gel (hexane/ethyl acetate 1/9 to 2/3) afforded 1.17 g (62%) of the product as brown oil. MS: m/e=222.2 (M+).

Provenance & Evidence