Hydrogen Bromide → 6-Butylaminomethyl-naphthalen-2-ol

Participants

Reaction Steps

A mixture of butyl-(6-methoxy-naphthalen-2-ylmethyl)-amine (10.0 g, 41.09 mmol), prepared in the previous step, 300 mL of 48% HBr and 200 mL of glacial acetic acid was refluxed under nitrogen for 19 h (overnight). The solvent was removed under reduced pressure. The resulting residue was partitioned between ethyl acetate and 5% sodium bicarbonate. The organic layer was separated, dried (MgSO4) and the solvent removed under reduced pressure to give 6-butylaminomethyl-naphthalen-2-ol (7.54 g, 80%) as a brown solid, mp 108-112° C.

Provenance & Evidence